Outfitting a Boat to Sail Around the World: What We Bought, What We Learned & What We’d Do Differently


Outfitting a Boat to Sail Around the World: What We Bought, What We Learned & What We’d Do Differently post image

When talking about our boat, Cheeky Monkey, I’m not one to rattle off stats like amp hours, watts, horsepower or, really, anything technical regarding the equipment we’ve had installed. That stuff just doesn’t excite me. At all.

In fact, if you asked me right now for a tour of the Orient Pearl and Ryan wasn’t around, I would most likely sit you down for a drink in the cockpit, show off how comfortable the space is, then I’d take you up to to our sun deck and show you the spectacular view. I might even make you another cocktail. And if you really wanted me to get technical, I’d show you how the espresso machine works and, possibly, the washer/dryer.

Any discussion that ventures beyond the general virtues of having an inverter (so I can make cappuccinos), a generator (so I can run the washing machine) and a high-tech spinnaker (so we can sail fast) will find me excusing myself from the room. “Go ahead and show yourself around…I’m just going to be over here, you know…zzzzzzz.”

So when a very excited couple motored their dinghy up to Cheeky Monkey one day and invited themselves on board for a tour, I cursed Ryan for not being there to save me from the mind-numbing boredom of showing an overexcited gear-head the engine room.

“Yep. That’s our diesel engine. Looks like every other diesel engine you’ve seen. Aaaand here’s the other engine. Yep, exactly the same.”

Normally I enjoy impromptu visits from random cruisers. We’ve met some extraordinary characters in anchorages all over the world, some of whom have become lifelong friends from the first encounter. Which is why I never turn down the chance to meet new people.

I also know that, at some point over sundowners, all conversations with fellow live-aboards will inevitably turn into a discussion about battery banks. Because life at anchor is all about batteries; they are the power source that keep everything running in our little floating homes. They’re what allow us to charge our laptops, power our electronic charts, make ice, refrigerate food and have I mentioned the espresso machine? There is also a multitude of methods for charging your batteries, which cruisers love to talk about. It’s like suburban homeowners getting together and comparing how often they have to mow their lawns and trim their hedges. Both are perfectly understandable, considering the demands of the lifestyle.

It’s just that the people I most enjoy talking to understand that conversations about battery banks come well after the introductory banter about where they’re from, how long they’ve been sailing, what they do for work, where they’ve sailed from, where they’re headed to and places they’d recommend visiting. You know, the kind of conversation that endears a new acquaintance to me before I have to forgive them for boring me with stats of their solar panel wattage and how we should consider getting one of those irritatingly noisy wind generators.

“Yoo hoo!” The two strangers cooed from their dinghy, causing me to look up from my laptop. “Hi! We just LOOOVE your boat! We’re thinking about buying one of these in a year or two.”

And before I could ask what their names were, I was handed a dinghy painter as the woman and her husband clambered onto the stern of Cheeky Monkey. “Do you mind if we come aboard for a little look?”

“Uh. Yeah, sure.” At a loss for anything else to say, I introduced Kristi, who was sitting in the cockpit working intensively on her laptop. She pulled her Beats headphones off her ears and looked at me quizzically as if to say “Are they staying long? Should I stop working?” I shrugged and said, “These guys are thinking about buying a Helia. I’m sorry, what are your names?”

“Jane and John.” Of course, those weren’t their names. But after spending an hour draining my brain of every mechanical detail short of a full wiring diagram for the boat, I completely forgot their real names.

“Right. Jane and John, this is Kristi.” I gestured towards the table. “Come on in, have a seat. Can I get you a drink?”

“Oh no, thank you. We won’t stay long. We really just wanted to have a look around, if you don’t mind. It’s such a beautiful boat.”

I looked at my watch to calculate how much time I thought would pass before someone made me open up the engine room and talk about alternators.

Forty-five minutes, it turned out. And there was no small talk or cocktails to ease me into it. Just forty-five minutes of the kind of rapid-fire questioning that made me feel like I was on the world’s dullest game show.

“Is this the owner’s version or the charter version?” – Owner’s version.
“What’s her cruising speed?” – 6.7 knots, on average.
“How big is your fuel tank?” – 500 liters.
“Your water tanks?” – 600 liters.
“How many watts of solar panels do you have?” – 900.
“Why did you get the flexible solar panels?” – They look nicer. And you can walk on them.
“But they cost more and they’re less efficient, I hear.” – They work for us.
“What’s this?” – The ice-maker. It doesn’t work.
“Don’t you have a freezer? Why do you need an ice-maker? – For parties, silly.
“You say it’s not working?” – Sore subject. I’d rather not talk about it.
“So you have a generator?” – Yes.
“Is it a Cummins or an Onan?” – It’s a Cummins/Onan.
“Really? I’ve never heard of that. Can I see it?” – Um, okay.
“Huh, look at that. A Cummins/Onan. Is that your watermaker?” – Yes.
“What’s the brand?” – Aqua-base.
“Never heard of it. Why didn’t you get a Spectra?” – I don’t know.
“How much water does it make?” – 60 liters an hour.
“Do you have problems with your mainsail? I’ve heard it’s tricky to pull down.” – Yeah, we added 3 cars to the mast. Problem solved.
“What brand?” – Z-Spar.
“That’s a very good brand.” – Yes, so I hear.
“Wow, a washing machine. Do you even use it?” – Yes. All the time.
“Do you like your davits?” – Not really. I wish they were higher off the water.
“Is it strong enough for that heavy dinghy?” – The dinghy’s not heavy. It’s aluminum.
“What make is it?” – AB.
“How long is it?’ – 10 feet.
“Is that a two-stroke outboard?” – Yes.
“How many horsepower?” – 25.
“25 HP! Do you need that much?” – Yes. We like to wakeboard. And go fast. Mostly just go fast.
“What kind of engines do you have?” – Volvo Penta.
“How many horsepower?” – 55.
“Wow, that’s a lot. Did you get the upgrade?” – I don’t know.
“I think the standard option is 40, so you must have gotten the upgrade.” – Okay. I don’t know.
“Can I see the engine room?”

BOOM. There it was. 45 minutes of being jack-hammered with questions and, finally, they asked to see the engine room. Surely this is the end of the tour, I thought, as I glanced at my watch. I was secretly wishing for a small galley fire or some other mild emergency to pull me away from the interrogation.

Thankfully, John must have spied the flutter in my eyes as they involuntarily tried to roll themselves into the back of my head because, finally, he said, “I just have one more question and we’ll leave you alone.” I nodded and exhaled. “We saw your blue lights from our boat last night and we were wondering if they were a factory option or if you added them.”

“We added them,” I said.

“But why? What are they for?” said John, showing genuine confusion.

“Ryan wanted them,” I said. “He’s from Essex.” I knew full well that my answer didn’t make much sense. But I didn’t care to explain the “boy racer” DNA that all East Londoners are apparently born with.

“Wasn’t it expensive? Seems like a waste of money for something so unnecessary,” said John, who was on a roll now. “I’d rather spend the money on more solar panels. You can never have too many solar panels. Except I’d install fixed panels, not these flexible ones. I’ve seen some boats where they’ve built a platform off the back of the roof so they can fit more solar panels. It’s a good idea, I think.”

“Yeah, but it looks like shit.” I said. Apparently, I’d lost my patience. “And it’s not cheap. Plus it looks like shit.”

“Who cares what it looks like when you have all that solar power? Anyway, that’s what I would do.” John said.

Now, it was clear early on that Jane and John probably weren’t going to become my new best friends, but that comment about the blue lights was the nail in the coffin.

Since when is fun a waste of money? Nobody spends a crap-load of cash on a quickly depreciating boat because it is a “sensible investment.” IT’S A FREAKING BOAT.

But of course, I didn’t say any of that out loud. I simply shooed Jane and John towards their dinghy as politely as I could, all the while checking my watch and making comments about the time, as Kristi looked up from her computer and tried not to laugh.

“That was intense,” Kristi said after our visitors were gone. “I’m super impressed. I couldn’t have answered any of those questions.”

“I made half of it up.”

Which is true. I asked Ryan, when he got back, how much water our tank holds and how many watts of solar panels we have. Apparently, the answer is 750 liters and 760 watts. Not 600 liters and 900 watts. Also, yes, the 55 HP engines were an upgrade from the standard 40. What the hell do I know?

Which brings me to my point: boaters (who are not me) love to geek out on gear. And there is no greater opportunity to dive head first down a rabbit hole of technological research than beginning the process of buying a new boat. And even though researching gear is most riveting when it’s your own future gear, I could not seem to muster enough interest to be of any use in this department.

This is why Ryan did all the research and ordering for the technical equipment we installed on Cheeky Monkey. Because, when pressed to make a decision about things I know very little about, I generally just go with the method I use for shopping at Ikea: cross off the cheapest and most expensive options and go for something mid-range and attractive. I have realized, however, that this is not a suitable method for selecting items like autopilots, anchor chain or battery chargers. But it is a perfectly appropriate method for selecting things like espresso machines, kitchen utensils, decorative cushions and linens. Therefore I have tried my hardest to stick to the areas where my methods are applicable, leaving everything else (as in, the bulk of the hard work) to Ryan.

Unfortunately, it seems the information most enthusiastically demanded of me by readers and YouTube subscribers alike is what technical gear we selected to install on Cheeky Monkey and why. My inbox is full of polite and enthusiastically written emails asking if I could — pretty please — itemize our purchases for Cheeky Monkey and briefly comment on how we decided on the products we bought.

And because I know there is no way to briefly comment on such long-winded decisions, I have unintentionally ignored all those emails and promised myself that one day, when I have more time and greater patience, I will write those lovely readers back and give them a fully formed response worthy of their attention.

Except those emails are still sitting in my Inbox, unanswered. Because technical talk bores me to tears. And because time just keeps slipping through my fingers.

So I am hereby issuing an apology and disclaimer to those who are like me (as in, you would rather spend an hour in the dentist’s chair than spend that hour talking watts and amps and the gauge of cable required to properly install a chart plotter) because I’m about to do what I have desperately avoided doing for a very long time. I’m going to give you a semi-comprehensive run-down of the major stuff we installed on Cheeky Monkey.

I’m going to tell you all about the stuff we love, the stuff we regret and the stuff we would have done differently if we knew then what we know now, after nearly a year of owning our Fountaine-Pajot Helia 44 catamaran. And because I have absolutely no ability to retain technical information, I will borrow Ryan’s expertise in this area. So, all thanks should be showered on him, not me.

It’s also worth noting that though this is a list of gear we ordered specifically for our Helia, most of the product research we did can be applied to any cruising boat, whether it be a monohull, a catamaran or a motorboat.

So to all you amazingly patient gear-heads out there, you’re welcome. This one’s for you. I hope it has been worth the wait.

To the rest of you, I’m sorry. I know this isn’t our thing. But the next time you have trouble sleeping, skip the Ambien and read this list instead. You’re welcome, also.

13 things we’re thrilled with (and would totally order again)

1. The boat


outfitting-boat-sail-around-world-cheeky-monkey.jpgCheeky Monkey in San Blas, Panama (Photo by Bruna Toledo de Arcangelo)

This is probably obvious, but it needs to be said: we LOVE our boat. There is no such thing as the perfect boat, of course, but there is the right boat for the journey you’re planning. And we definitely made the right choice of boat for us and this round-the-world trip.

The main things we love? The comfort and the performance. Even with crew on board, having upgraded from a 34-foot monohull, we feel positively spoiled for space. And contrary to common lore about catamarans, the Helia sails beautifully – she’s fast and light, especially going downwind, and she’s not that bad pointing upwind, either, though it’s not Cheeky Monkey‘s most comfortable point of sail. Yes, there is some slapping of waves under the hull when beating into rough weather, but it’s no more disturbing than what we’ve experienced on monohulls in stormy conditions. Also, we love the modern layout, the brightness and the incredibly spacious and comfortable cockpit, which is where we spend most of our time on board.

For us and this journey sailing around the world, the Helia is about as perfect as a boat can get.

2. Battery charger upgrade + 2nd battery charger

Remember when I said all cruisers’ conversations eventually lead to discussing battery banks? Well, part of that discussion involves battery chargers and inverters and…zzzzzz.

Oh dear. So sorry. It looks like I fell asleep while typing. I think it’s probably best if I turn this bit over to Ryan to explain. Because when it comes to battery chargers, I just…zzzzzz.

Here’s Ryan:
“When I asked our broker what the options were for the largest inverter/charger available, he said Fountaine-Pajot could only install a 1000-watt combination inverter/charger with a 60-amp battery charger. Which is fine if you’re just a weekend sailor or a charter boat that lives in a marina. But, living full-time on anchor and sailing around the world, I didn’t want to have to run the generator or the engines all day to fully charge our batteries.

So I worked out what I wanted, which was a 3000-watt inverter with a 120-amp battery charger. But I couldn’t get that through FP, so I had to go with their standard option and then install my own inverter/charger later. Our post-factory outfitter found me the Victron inverter/charger I wanted — basically the biggest one I could buy — and then bought the FP-installed inverter/charger off me.

Later, I ended up buying a second 60-amp battery charger — ironically, the same one I’d sold. Why? Because our batteries will take up to 200 amps. So I figured why muck about with less?”

3. Permateak floor in cockpit

Fountaine-Pajot offers 3 options for the cockpit deck: plain non-slip fiberglass, teak wood and Permateak (fake teak).

The one option we ruled out was the fiberglass, as we felt it made the cockpit space too white and forever in need of scrubbing (I always opt for less scrubbing). Also, we liked how the wood floor felt underfoot, as well as the way it looked; it breaks up the overall whiteness of the boat and camouflages dirt and smudges (again, less scrubbing).

But this was definitely one of those things we might have ordered differently if we hadn’t gone to a few boat shows and talked to a few different owners about their choices. Without consulting anyone, I probably would have opted for the teak because I love wood (so long as it doesn’t require varnishing). But we met a Helia owner with a badly stained teak deck that he regretted ordering because it required so much maintenance. He said with kids and guests spilling everywhere, it wasn’t long before the teak looked terrible.

Then we saw a boat with Permateak laid in the cockpit, which we thought looked nice, and we spoke to the owner who said he’d bought his boat with a teak deck and then had it all ripped out because after just a year it looked so bad. He said the Permateak was an improvement because it was lower maintenance and it looked brand new after a year, despite the same amount of spills and traffic. There is a drawback to the Permateak, which is that the surface absorbs more heat than its real teak equivalent. But as the flooring is only laid in the cockpit, which is shaded from the sun, this has never been an issue for us.

After a year on board, I’m so happy with our Permateak deck that I’ve considered having the same material laid on the floors of our heads, since the white non-slip surface always looks dirty to me (and, as I mentioned, I hate scrubbing). But, really, I should have thought of that back when the boat was in France. Now that we’re on the move, it seems unlikely that I’ll get this done anytime soon.

4. Parasailor (spinnaker – 156 square meters)


parasailor-outfitting-boat-fountaine-pajot-cheeky-monkey.jpgThe “Big Banana” in all its glory (Photo by Kristi Wilson)

This sail, made by a company called Istec (not offered by Fountaine-Pajot), is just plain amazing. Though it is expensive, it has become a crucial piece of kit on board Cheeky Monkey for crossing oceans with speed and comfort. Not to mention, it looks totally badass.

I wrote an entire blog post on our Parasailor when we first got it, but now that we’ve had a year’s experience using it, here are some statistics so you can judge whether this sail is of any use to you:
It’s a dead-downwind sail only: despite what salesmen have told us about the Parasailor being able to handle true wind angles ranging from 180 degrees to 60 degrees, we’ve only been able to use this sail between 160-180 degrees. Maybe it was a typo? Perhaps they forgot the ‘1’ in front of ’60’ degrees?
On a dead run, you can’t beat this sail for speed. Crossing the Atlantic, we were easily clocking 10-13 knots in 18-25 knots of apparent wind.
Our top boat speed was 17.9 knots with the Parasailor, surfing down a wave on the Atlantic.
It’s a great light wind sail, too. We get 4 knots of speed in 5 knots of apparent wind.
Incredibly stable, low-maintenance sail to operate: the super handy “snuffer” sock allows you to hoist and drop the sail single-handedly (though it’s even easier with two or more sets of hands), unlike other types of symmetrical spinnakers. The hole or the “wing” at the front lifts the sail up and keeps it filled, which means there is very little work required on the sheets to keep the Parasailor flying. We’ve had our Parasailor up for nearly a week and barely touched the sheets during that time.

5. Genniker (with bowsprit addition)


outfitting-boat-genniker-sail-around-the-world.jpgIf I had to choose just one sail, this would be it

Fountaine-Pajot installs a bowsprit if you order the furling genniker (also called a screecher) from them, which is great because it means your warranty for the sail and the bowsprit is held with FP. We’ve had endless nightmares trying to get warranty work done on our non-FP orders, so it’s always a relief when something breaks and we find out it’s covered by FP.

Here’s how versatile this sail is:
It’s great in light winds (anywhere from 5-15 knots apparent) at a wind angle of 90-130 degrees with the mainsail up. Any more downwind than that and the mainsail blankets the genniker.
We’ve recently discovered a new trick with this sail, which allows us to sail with the wind at a 120-150 degree angle, a window we previously had no sail for. We detach the tack from the bowsprit and bring it over to the Parasailor block on the windward bow. And then we use a barber haul tied to our mid-ship cleat to pull the sheet downward. Note: we have no idea if we’re meant to even do this with the sail, as we’ve just invented this configuration. But as it is working for us, we’re going to keep at it until someone gives us a valid reason not to.

If I were to buy only one extra headsail to go cruising with, I would go with the genniker (screecher) because of its versatility. Of course, you can get by with just the jib as a headsail, but we use our genniker as much as (if not more than) our jib. So if you have the extra cash in your budget, this is the sail I would go with.

Now, if you’re looking to fully kit out your boat, and you can afford the $13,000 price tag, I would absolutely recommend buying a Parasailor. Especially if you’re planning to sail around the world with the trade winds. There is nothing more enjoyable than sailing fast downwind with a no-fuss spinnaker that requires little to no trimming. It’s an incredible ride.

6. Extra blocks for sails

It boggles the mind how many additional blocks (pulleys) we’ve ended up adding to Cheeky Monkey. The Parasailor required ten additional blocks, the genniker needed seven additional blocks and we also added a block to each reefing line on the mainsail to help them run better. So, in total, we’ve added twenty blocks to the boat since we bought her.

And, crazily, we use them all.

7. Additional winch

For some reason, with the genniker headsail and bowsprit installation, Fountaine-Pajot includes a Lewmar 45 winch on the port stern for the port sheet, but they don’t include an additional winch on the starboard side.

If we didn’t install another winch, we would have had to use one of the winches at the helm for the starboard genniker and Parasailor sheet, which is strange because that would make the angle of the sheet to the winch drastically different from that on the port side. Also, it would mean the sheet cuts across the walkway along the starboard hull, preventing anyone from leaving the helm to go forward while on a port tack.

So instead of settling for that option, we ordered an additional Lewmar 45 winch to be installed on the starboard stern, parallel with the port winch.

These winches are essential for manning the genniker sheets and also the Parasailor sheets and guys. I couldn’t imagine being as happy with our set-up if we were running all our starboard headsail sheets to the helm, so this post-factory addition is something I’m now grateful for.

8. Barbecue upgrade


outfitting-boat-sovereign-bbq-catamaran.JPGMy prized Sovereign BBQ alongside our custom outboard hoist

Remember how I said my method of shopping is to go for the mid-range option (not too cheap, not too pricey) that looks the most attractive? Well, that applies to pretty much everything but cooking appliances.

What can I say? I like to have nice things to cook with.

And it’s not because I’m a fabulous chef or I take an extraordinary interest in the culinary arts. It’s just that food and cooking has a become a much larger part of my life on a boat than it ever was on land. Living in New York City, I could count on one hand the number of times I cooked at home in a year. Living on a boat, we cook all our meals. And my favorite meal? MEAT. As in, grilled steak, grilled chicken, grilled ribs, grilled fish…you name it, I’ll grill it.

Which brings me to my favorite accessory on the boat besides our espresso machine. It is our state-of-the-art Sovereign barbecue propane grill, which is manufactured in Australia, a country of people who know a thing or two about barbecues. And one of its best features is that it’s plumbed into our main propane line, so all I have to do is flick a switch and my barbecue is alight and ready to go.

I’m sure the standard Fountaine-Pajot grill option would have been fine if I never knew what life was like as a discerning connoisseur of barbecue grills. But, now that we’ve experienced cooking with the Sovereign, I don’t think my life on board would be complete without this incredible piece of culinary engineering.

9. Washer/dryer

When we lived on our old Catalina 34, the most time-consuming of our regular housekeeping tasks was collecting water from shore and doing laundry (as in, bagging up two weeks’ worth of clothes, schlepping it all to shore, tracking down a laundromat, if it existed, and then sitting around for a few hours waiting for the machines to finish before schlepping everything back to the boat).

So when I found out we could have a washing machine on board Cheeky Monkey, I was doing cartwheels for joy.

The trick, however, is finding the right machine to fit the space provided. We selected an LG combo washer/dryer unit which fits perfectly into the space across from our linen closet in the owner’s cabin head. Granted, we rarely use the dryer function since our clothes dry so quickly in the sun. But the washer has a 30-minute speed wash function that uses an amazingly minimal amount of water, which is great because, as you know, water is precious on a boat.

To give you an idea of how much I love having a washing machine, if you told me I had to give up either my Sovereign barbecue or my washing machine, I’d throw that barbecue overboard without hesitation. But the dryer function? I could probably live without using 3 hours of electricity to turn my pile of wet clothes into a pile of hot, damp clothes.

10. Custom-designed outboard engine hoist and mount

When we sailed Cheeky Monkey out of La Rochelle, France for a 1400-mile shakedown cruise, we didn’t want our outboard engine bouncing up and down with the dinghy hanging off our davits, especially with the way our davits sit so low to the water. But the mounting plate we ordered for our outboard was on backorder and the whole of France was going on vacation for a month.

So instead of waiting around for a month for our mounting plate, we used a halyard to lift our very heavy 25 HP engine into the cockpit and laid the outboard down on its side, wrapping it in a heavy mat and tying it down for our trip. This was a makeshift solution and not a long-term plan for passages, but we weren’t sure yet what the ideal set-up would be for transferring our outboard from the dinghy to the mounting plate.

Once we got to Menorca, we hired Pedro’s Boat Centre to do the work we couldn’t get done in France, which included installing a mounting plate on our stern rails for the outboard. Ryan also decided he didn’t like using the halyard to hoist the engine, so he collaborated with a metal worker to design a reinforced pulley hoist on the stern so we could lift our outboard off our dinghy using the electric winch on the stern.

To get the hoist to work with the outboard, we also hired a canvas guy to design and sew a cover for the outboard which had a sturdy strap for lifting. And all of this work went smoothly because Pedro and his guys were incredibly good at what they do.

The fact is, if you can find the right expertise, you can design almost anything you want for your boat. You can do what Ryan did and sketch out on paper what you want, then find a guy to build it for you in a way that’s structurally sound.

But if you don’t trust the guys working on your boat, leave the complicated stuff until later when you can find the right people.

11. Generator / air conditioners

For reasons we could not control, we have the largest generator known to man or boat. It’s a Cummins/Onan 8.5 kilowatt generator, which was installed by Fountaine-Pajot as part of the standard package that comes with the boat when you order air conditioning.

From what I can tell, if we had not ordered AC, we could have gone with a much smaller generator, which would also have weighed a lot less. At the time, we hemmed and hawed about whether to get the AC, since we hated the idea of having such a big generator weighing down the foredeck. But then we also knew we would be sailing to a lot of hot countries and the idea of ducking out of the scorching sun and stepping inside the air-conditioned cabins sounded like a luxury we could get used to.

The crazy thing we couldn’t understand was why FP insisted on installing six air conditioners (two in each hull and two in the saloon). If we had a choice, we would have gone with one air conditioner in each cabin and one in the saloon (four in total), but we didn’t get a choice in the matter. It was either all six air conditioners, or no air conditioning at all. And if we wanted the air conditioning, we had to get the bigger generator.

So even though we think six air conditioners and an 8.5 kilowatt generator are a bit overkill, the fact is we like our air conditioning, so any complaints you hear on the subject will be made from inside a climate-controlled cabin while sipping a cocktail.

12. Ground tackle

When we outfitted our Catalina 34 to go cruising, we replaced our Danforth anchor, which served us well in the sand and mud-bottom harbors around New York, with a Rocna 20 (44 lbs.) which essentially changed our life at anchor. Though the Danforth was fine in the Northeast of the U.S., it gave us a few sleepless nights from dragging as we sailed further south towards Florida and the Caribbean. Our Rocna, however, never moved. Not even once. We slept like babies.

After that experience, the Rocna 40 (88 lbs.) was the obvious choice to go with for Cheeky Monkey. But we also got a 66 lb. Mantus anchor for a back-up because, while it has the shape and effectiveness of the Rocna, it packs up small once it’s disassembled. We’ve laid ours in our anchor locker and it fits there perfectly in case we need to throw out a stern anchor or if something should happen to our Rocna.

But as we learned with our first Rocna purchase, the real investment isn’t in the anchor; it’s in the chain, which costs about 3 times more than the anchor itself, if you’re springing for 100 meters. And that’s just for your standard 12 mm stock, which is what Fountaine-Pajot recommend, since the gypsy on the windlass is designed for 12 mm chain.

After weighing up the options, however, Ryan was concerned about weighing down the bow of Cheeky Monkey and negatively affecting its performance, especially since the foredeck was already burdened by the weight of a massive generator. The fact was 100 meters of 12 mm chain would add 900 lbs. to an already heavy forward load, which sounded like an awful lot.

But as with everything else we looked at buying, Ryan wouldn’t rest until he’d explored all the options in the universe. Which is how, in his research, he came across a different kind of chain — something called high-tension chain. Personally, I never would have found such a thing because I would have just assumed that standard chain is what everyone got. “Sure, 900 pounds sounds awfully heavy, but if that’s what it weighs, then that’s what it weighs.” That’s why I wasn’t in charge of buying the chain.

Ryan, on the other hand, said to himself, “What if someone somewhere invented a stronger, more lightweight chain… [*Googling furiously*] Oh, look at that! They have!”

And that’s how we ended up buying 100 meters of 10 mm G70 high-tension chain, which only weighs 510 lbs but has the strength of the standard 12 mm chain. The only problem was that we had to change out the gypsy on our windlass at an additional expense. Also, the G70 chain is pricier than standard chain (like everything new in technology). But as we’d sheared off nearly 400 pounds of weight from our foredeck, Ryan was happy. And I knew no different, so I was happy anyway.

13. Blue lights


sail-around-the-world-cheeky-monkey-blue-lights.jpgCheeky Monkey showing off in Port Vell, Barcelona

Last, but definitely not least on this list of loves, is our infamous custom blue lighting package.

When Ryan explained to our post-factory outfitter, Pierre, that he wanted to have blue “party lights” illuminating the deck as well as blue lights under the hull, Pierre looked at me with confusion. “But why?”

“It’s difficult to explain,” I said. “Have you ever seen the TV show ‘Pimp My Ride’?”

Pierre furrowed his brow. “I don’t understand, but whatever you want, we can do it.”

And so we had blue party lights installed on the deck of Cheeky Monkey, which actually come in handy at night when we’re sailing in fickle wind and we want to illuminate the sails without losing our night vision. The underwater lights, however, have no other function than to make people say “ooh” and “ahh”.

When you’re standing on the back of our boat shouting, “Ooh! Look at that shark!” you’ll understand.

2 things we regret

1. Ice-maker

If you’re a regular visitor to this blog, then you know why this damned ice-maker is #1 on my list of regrets.

But, if you’re new to the Saga of Dashed Dreams, aka The Little Ice-Maker That Couldn’t, then let me give you the 10-second summary.

Once upon a time, there was a Vitrigo 12-volt ice-maker that promised to make Ryan’s cruising dreams come true…

The problem was that Fountaine-Pajot didn’t offer an ice-maker for the Helia. So our broker added “ice-maker” to our list of post-factory installations and assured us he’d installed similar machines on a great number of other boats. Great! Ryan did a little dance and imagined himself hosting parties and making cocktails with an endless supply of ice.

Then one day, the ice-maker arrived. And, as it was being installed, Ryan sat patiently nearby, waiting to try out his new toy. Except it didn’t work. The ice-maker would get cold, but it refused to make ice.

This prompted some probing around inside the machine, which dug up a piece of broken plastic, causing the installers to stand around the ice-maker for a while, scratching their heads and smoking cigarettes. No one could identify whether the broken plastic part was the reason why the ice-maker wouldn’t work and so, instead of replacing the machine, our outfitter spent the next few months ordering random parts to be mailed without instructions to various ports where we were docked. Meanwhile, we ran around hiring refrigeration experts to look at our ice-maker and install the parts we were sent.

Fast forward 8 months: The ice-maker still doesn’t work. Eventually, we are told Vitrigo stopped making our model of ice-maker in the 8 months that passed and therefore a replacement cannot be ordered. Our broker offers us a refund, which we take in lieu of having him order another brand of ice-maker which we would no doubt spend another year chasing after him for.

After all this hassle, it has occurred to me if we’d just gone for the standard beer fridge option offered by FP, instead of the non-standard ice-maker in the cockpit, we wouldn’t be telling this sad story over and over again. But we just couldn’t see the point of a tiny little fridge that would essentially save us from having to take two extra steps into the galley to get a beer out of the main fridge.

But who am I to criticize? We basically opted for a machine that would save us from having to fill up our own ice trays from a faucet. And, as a slap in the face, it won’t even do that.

2. Extra sleeping quarters (forepeak cabin & mattress)


outfitting-boat-sail-around-world-fountaine-pajot-helia.jpgOur friends’ daughter, Ellia, loved her forepeak cabin (Photo by Genevieve Stolz)

Fountaine-Pajot offers an option to convert the port forepeak storage space into a small cabin with a fitted mattress, a porthole and a reading light. And we went for this option because we thought it would be a great space for a couple and their kids, since the forepeak cabin is just ahead of the forward port cabin. Plus, when I looked at the cozy little cabin in the forepeak, I imagined if I were a kid on a boat, that would be my favorite place to sleep.

The reality, however, is that we use that forepeak primarily for storage. We stow the genniker there when we take it down and we store extra supplies in that space when we’re provisioning for ocean crossings.

But because we opted for the cabin, we got stuck with a terribly leaky porthole, which we wouldn’t have had otherwise and which has caused us no end to problems with seawater pouring in through the seals when we’re underway. We now store the mattress in a body bag we ordered online (who knew you could order body bags online?) for the sole purpose of keeping the mattress dry from the water that constantly drips in through our porthole.

It’s only with hindsight that we could know that the forepeak cabin would rarely get used for sleeping quarters because, in all practicality, there are more comfortable spaces to sleep on the boat if all the cabins are occupied. The saloon settee is one such spot, as is any one of the cushions in the cockpit or up on the sun deck, when the weather is warm.

We also could have opted to have a dinner table in the saloon (instead of the coffee table we ordered) which converts into a double bed, but we had to ask ourselves just how many overnight guests we would even want to cram onto Cheeky Monkey at any one time.

On the Shoreseeker Challenge across the Mediterranean Sea, we discovered that we could fit fifteen crew on board for four days in an emergency, but that was far from ideal. We think the maximum number of crew we can fit comfortably on Cheeky Monkey for long passages is six. We could fit more than that for a weekend or two, but for long-term sailing, we probably wouldn’t.

Basically, if we were to redo our order for the boat, we would have just kept the forepeak space for storage and not added a leaky porthole to our list of boat problems.

2 things we would’ve done differently (if we knew then what we know now)

1. Autopilot(s)

The only Cheeky Monkey saga that has rivaled the frustrations of our ice-maker is the trouble we’ve had with our autopilot.

To make a long story short, we bought a Garmin autopilot for Cheeky Monkey because we’d had a bad run with our Raymarine on our old Catalina 34. What we didn’t know was that Raymarine had come a long way since then, blowing Garmin out of the water with their new 9-axis gyroscopic compass thingy…I’m not really sure what it’s called or how it works; I just know it’s amazingly accurate.

But never mind the technicalities. And let’s skip over the story of the faulty Garmin installation, the multiple repairs, and the final realization that the Garmin, even when correctly installed, steers like it’s drunk, and get to the point: we now have two autopilots on board Cheeky Monkey. Because after all the trouble we had with our Garmin, we decided to install a Raymarine as our primary autopilot and relegate our Garmin to the back-up in the event that we lose our autopilot; something we have a great deal of experience with. I have clocked just as many miles hand-steering as I have with a working auto-pilot, so I knew the risk was real.

And thank goodness we installed a second autopilot because we have yet to cross an ocean with both of our autopilots in tact. On the Atlantic crossing, the “no drive detected” errors on our Raymarine increased in frequency to the point where we had to steer the rest of the way using our Garmin. And, case in point, while I was literally writing this post in the middle of the Pacific Ocean, our Raymarine suddenly decided it only wanted to steer to starboard, causing us to jibe in the middle of the night. So we’ve shut down our Raymarine and turned on our Garmin which, for all its faults and our complaints, has never actually broken on us. In fact, it’s only ever saved us when our Raymarine has ceased to function, so perhaps I should say nicer things about it.

There’s an accidental lesson in all of this: never cross an ocean without a spare autopilot, unless you’re prepared to hand-steer the whole way across. We never had a spare autopilot on board Hideaway, but then we never sailed for longer than three days without stopping, so hand-steering in a bind was never that big a deal.

But if we only had one autopilot on board Cheeky Monkey right now, which was the original plan, I’d be hand-steering for six days while trying to type at the same time. Which sounds awfully tedious.

I guess now I should say we were lucky our Garmin was so crap to start with because if we’d only ever known a working autopilot, we never would have thought to install a second one.

2. Aqua-base 12-volt water-maker

Back when we had to schlep all our water back and forth from shore in leaky five-gallon jugs, we would protect each drop as if it were a gold nugget. I got good at washing a sink full of dishes with two cups of water and I could go a week without showering.

But now that we can make our own water, and we have crew who have never known a life without free flowing faucets, we get through about 150-250 liters of water a day. But the upside of that is we smell a lot nicer.

To replace all the water we use, we have to run our water-maker for about three to four hours a day because we only have the capacity to produce up to 60 liters an hour. Which was a bit of an oversight, really, because it turns out we didn’t get the biggest water-maker available.

While our water-maker only produces 60 liters an hour, Aqua-base makes the same unit but with two membranes, which produces 50% more water in the same amount of time, therefore taking 35% less time to do it.

So, why didn’t we get the bigger water-maker? I really have no idea. It’s possible that we got so caught up in trying to decide if we should get a DC or AC-powered unit that we forgot to ask whether it was even possible to get more than 60 liters an hour out of a water-maker. I know there was an overwhelming amount of research involved in outfitting our boat, so it’s not surprising that some information slipped through the cracks.

But the good news is that we made the right decision with a DC-powered (12-volt) water-maker because it means we can make water anytime we want and not just when we’re running our generator. We probably couldn’t have known this before we got out on the water and started actually using the systems we installed, but it turns out we don’t run our generator nearly as often as we run our water-maker. We might turn our generator on for about an hour and a half each day, but we run our water-maker for at least three hours a day when we’re cruising full time.

In hindsight, we should have asked ourselves if there was any reason why we wouldn’t want to make 100 liters an hour rather than just 60. The answer would have been “no.”

2 other modifications we ordered (which we love)

1. Instruments moved for better visibility


outfitting-boat-sail-around-the-world-garmin-instruments.JPGWe wanted our instruments in view of the cockpit, not hidden behind the helm

Fountaine-Pajot offers a few different electronics packages for the Helia, but the problem for us was we couldn’t control where our instruments would be installed and we didn’t like the spot where they wanted to install them. Strangely, the instruments get installed behind the helm about parallel with your knees if you’re sitting down, which means you can only see the instruments if you are sat directly behind the wheel, looking down, with your legs apart…so long as you’re not wearing a skirt.

To us, this was not ideal because the luxury of having an autopilot is that we don’t always have to be sitting behind the wheel. We wanted to be able to see our boat speed, wind speed, wind angle, depth, etc., from the cockpit and the helm, not just when reclining at the helm and squinting to read the numbers near my knees.

So we declined to order our electronics through FP and instead had our instruments installed by our post-factory outfitter in a much more ideal spot (for us). Now, as we’re walking around the boat, going about our daily business, we can look up and see the boat speed and whether the wind has shifted from anywhere in the cockpit.

2. Additional electrical outlets

When buying an older boat, I expect to find systems in desperate need of an upgrade, like energy-sucking halogen lights and a gross shortage of electrical outlets. But when buying a brand new boat, I fully expect the manufacturers to take into account the needs of the average blogging, YouTube creating, virtually connected New Yorker and provide the appropriate number of electrical outlets.

Or maybe I’m underestimating where on the spectrum I fall when it comes to how many electronic devices the average person has in 2016.

In my mind, if you’re under the age of 60, you own and regularly use, at minimum, a cell phone, a music-playing device (like an iPod), a computer and some kind of tablet (like an iPad) or Kindle, or both. And that’s not including the other rechargeable devices most people own at least one of, like cameras, electronic watches (like an Apple Watch or Fitbit), electric toothbrushes, portable shavers, wireless headphones and portable speakers.

If that’s right, then Fountaine-Pajot has grossly underestimated how many AC and DC outlets a modern human needs to survive in this world.

Which is why we took the liberty of installing five additional AC outlets — one at the nav station, two in the galley, one in our medicine cabinet and one in our “media cupboard,” where we store all our camera equipment and batteries. I mean, the fact that there are no electrical outlets in any of the heads seems like an oversight, at the very least.

We also added two more DC outlets — one at the helm (with a waterproof cover) and one inside our nav station desk, where we plug in things like our hand-held VHF radio.

And you know what? It’s still not enough. We’d like to add a waterproof AC outlet in our cockpit because, after living on the boat for a year, it turns out the cockpit has become our favorite work space at anchor. Yet there’s nowhere to plug in, so it means we have to keep going inside to charge our laptops. First world problems, I know. But they’re problems nonetheless.

Onboard communications: 3 recommended devices

If you’re still awake and reading, I am immensely impressed with your stamina. Because I fell asleep at least 7 times while writing this. No, seriously. This post is so long it has taken me a week to write. So, there’s no doubt you deserve a bonus for sticking it out until the end.

Which is why I’m going to let you in on the secret to our onboard data and communications — you know, how we download weather while we’re at sea, how we access the Internet while in port and, basically, how we remain in touch with the outside world as we’re sailing across oceans.

Okay, so it’s not exactly a secret, but it is one of the most common questions we get about the boat — how do we communicate, post on social media and get weather updates when we’re sailing?

And I have the answers to those questions. In fact, I’d like to offer you a rare piece of insight into the wide and confusing world of communications options for boaters, based on months of our own research, which came about after we were given a quote for a comprehensive WiFi and onboard data system that would cost us $20,000.

TWENTY THOUSAND DOLLARS! I mean, what?! Okay, look. We may be the kind of folks who don’t mind spending a little extra cash for fun accessories like blue lighting and an ice-maker. But we don’t just go throwing money overboard for the sheer hell of it. So unless that $20,000  included 10 years of unlimited data, I was always going to seek out an alternative option for getting online while sailing around the world.

Because here’s the thing: I know sailing is all about disconnecting, becoming one with nature and removing yourself from the pressing obligations of mainstream society. But let me just be honest: I am a writer with an online blog, a YouTube Channel, a dozen social media pages, a few different web sites and the occasional magazine deadline. In order to do what I love, I require quite a bit more time on the internet than the average person. And yet my access to the Internet is painfully minimal because I am constantly either at sea or trekking around a remote island, waving my iPhone around like a lunatic, trying to get a signal.

So here are the solutions we have settled on after extensive research, and after we worked out that the $20,000 proposed communications system was essentially just a bunch of cheap solutions installed simultaneously and then labeled as a “custom package” with a ridiculously high price tag. So we skipped the “expert” middle man and just bought and installed each component separately for a mere $2,500. I mean, seriously, with that kind of savings, we could buy and install an ice-maker in every cabin on the boat!

But let’s not get carried away. Here’s how we built a $20,000 system for a mere $2,500:

1. Badboy WiFi extender

On our last boat we had a Rogue Wave WiFi booster that served us pretty well for connecting to WiFi signals on land from the boat.

And the Badboy does essentially the same thing as the Rogue Wave, but we find it easier to use. It is connected to an antenna that runs up our mast, so we can connect to WiFi from a greater distance. The way it works is you log into Badboy’s IP address www.badboy.xtreme from any device and then you scan the list of available WiFi signals, which are either unlocked WiFi connections or connections for which you know the password, like nearby bars and restaurants you’ve visited. If the signal is strong, you can do work from the boat without having to sit in a bar spending money on food and drink to use their WiFi.

When this works, and the Internet is reasonable (after all, it’s never fast), you don’t have to worry about all the other solutions on this list because you’ve got unfettered free access to the Internet. Congratulations!

Note: This only works within about a one-mile range from land.

2. Pepwave Router

When the Badboy shows no available WiFi options, we move on to the next solution for accessing data, which is to use our router with a mobile data SIM card. We have the T-Mobile International Plan, which gives us unlimited 2G data anywhere in the world (almost — it didn’t work in Morocco), so we can pop our SIM card into the router and get slow but reasonable Internet data from local mobile phone towers.

Or, if you can track down a local pay-as-you-go SIM card, that’s even better because usually the Internet is faster and pretty affordable. We’ve found the going rate for data is $10/GB in most countries around the world.

Note: You can buy and use any normal router — it doesn’t have to be a Pepwave. This option also only works near land within range of a mobile phone tower.

3. Iridium Go! Satellite Phone

I can’t wait for the day when satellite data connections are so fast and affordable that we can stream Netflix via space while in the middle of the Pacific Ocean. That day has not yet come, but it is pretty amazing how accessible and affordable satellite technology has become in the last few years, so there’s hope yet.

When we bought our first satellite phone — the Iridium Xtreme, the best device Iridium offered at the time — we paid a lot of money both for the phone (about $3,000) and the data ($650 for 500 minutes which, annoyingly, had to be used in a 12-month period or they would expire). And then Ryan learned the hard way that the Iridium Xtreme wasn’t waterproof when he sunk his boat on a mad adventure sailing an ngalawa (local fishing boat) up the coast of Tanzania.

Ryan survived, as you may have guessed, but it meant we were down a satellite phone. So, when we bought Cheeky Monkey, we decided it was time to update our research and find out how much technology had improved since our last SatPhone purchase. And luckily for us, Iridium had just released a new and more affordable satellite “hotspot” called the Go!, which allows users to connect to Iridium satellites via an app on their smartphone or iPad.

So what can I do with my Iridium Go! at sea? I can’t stream Netflix, or even browse a website. But I can use my iPhone to download weather gribs and open them in our Weather 4D app (there are many weather apps you can choose from), I can send and receive emails and (small) photos, I can tweet, I can make phone calls at the rate of $1/minute anywhere in the world and I can transmit an SOS in an emergency. Plus, the best part about this little device is it only costs about $800, which is a big drop from $3,000, and unlike the inflexible data packages of the Iridium Xtreme, the Go! offers an unlimited data package for $135/month, which can be cancelled at any time.

I do have one rather specific piece of advice regarding cancelling the unlimited plans, however. When you buy the Iridium Go!, you should request as many SIM cards for the Go! as the company is happy to send you. The reason for this is that, yes, you can cancel your plan at any time without penalty, but to reinstate the same SIM card costs a silly amount of money (I can’t remember the exact amount), whereas if you throw the SIM away and activate a new one, it only costs $25 to activate a new card. With this method, you can activate your monthly plan just for the months when you are planning to be at sea, but cancel the plan for the months when you plan to stick close to land and have access to WiFi.

It’s because of these 3 devices — the Badboy, the Pepwave router and the Iridium Go! — that I manage to stay connected to the virtual world as well as anyone who lives at sea could possible hope to. And, thankfully, we didn’t have to spend $20,000 to acquire this system.

Plus, now you know how to build your own “custom” communications system on the cheap. See, aren’t you glad you kept reading?

Final thoughts

Though this rather extensive list covers most of the big stuff we ordered for Cheeky Monkey, it is by no means comprehensive. Beyond what you’ve read here, months of research went into products we didn’t end up buying, we made a million and one little tweaks that are too small to mention and we spent countless hours overseeing workmen to keep them from drilling holes in the wrong places, which they were wont to do.

In short, we found the process of outfitting our boat to be exhausting, incredibly time-consuming and almost as stressful as the full-time jobs we left in our wake. Which I have since learned could have been avoided, had we done more research on brokers before we started. But we liked our broker — he was a nice guy and we liked talking to him — so we assumed he had sold enough boats to know the pros and cons of the options offered by Fountaine-Pajot and that he could make recommendations based on our cruising plans, past customer reviews and his own research into the options he was selling.

But it turns out we made a few too many assumptions. What our broker didn’t know and couldn’t help us with was what ate up all of our time and energy as we pored over the purchases made by other FP owners who were kind enough to share with us what they’d learned.

Therein lies the problem: the broker you decide to work with can make or break your buying experience. And yet it can be difficult to know the good brokers from the bad brokers before you start working with them.

My advice? Get a recommendation from someone you trust or someone who has bought a similar boat to the one you’re looking to buy. Who did they use? What was their experience? Get some opinions before signing over your hard-earned cash and your dreams.

Also, I would go with experience. The high-volume yacht brokers out there often get a lot of business because they’re good at what they do. Plus, the advantage of going with a broker who sells dozens of the same boat make, year after year, is that he knows his stuff. All those questions we had about the pros and cons of DC and AC water-makers, the type of battery charger we needed and the type of anchor chain to buy? A good broker would know the answers because he’s already researched it for a dozen other customers and gotten feedback on whether or not they made the right choice.

That’s the key — a good broker doesn’t just place your order and then walk away with his commission, leaving you to fend for yourself. He saves you time and, hopefully, a lot of headaches by giving you well-researched recommendations, being responsive to your needs and handling your warranty issues when they come up.

Consider this: there is an overwhelming amount of stuff that you can’t even begin to ask your broker because you don’t know all the things you don’t know. All you know is the stuff you’ve thought to ask questions about, which may only be a fraction of the issues you actually need to address in order to get the complete boat of your dreams. It’s like that thing Donald Rumsfeld said about Iraq in 2002: “There are known unknowns; that is to say we know there are some things we do not know. But there are also unknown unknowns — the ones we don’t know we don’t know.”

A good broker doesn’t just deal with the known unknowns, the questions you have thought to ask about what you need to know. A good broker can enlighten you on the “unknown unknowns,” the crucial stuff you may not have even considered because, like most buyers, you don’t know everything about the boat you’re buying or the lifestyle you’re about to plunge yourself into. A good broker has sold dozens of the same boat with dozens of different configurations designed for long-term cruising, weekend sailing, chartering, etc., and has taken into consideration what your plans are with the boat and anticipated what you might need to make it happen. A good broker pays attention to details and will tell you why you might want to opt for the 100 liter/hour water-maker over the 60 liter/hour water-maker if you’re planning to sail around the world. And you want that broker.

As you can tell, Ryan and I have learned a thing or two in the process of buying and outfitting our boat, which is why I didn’t want to waste all that hard-earned knowledge by keeping it locked inside my head.

My hope is that this list helps someone out there find the answers they’re looking for as they pore over marine catalogs trying to figure out how best to spend their money.Save

Sailing Across the Pacific Ocean


Changing Course: Sailing Across the Pacific Ocean post image

I am not a natural-born sailor. The sea doesn’t call to me and I don’t crave the salty air.

What I love is land; I love seeing long stretches of road from my window, mountains outside my doorstep and tall trees silhouetted against the sky.

But that isn’t to say that I don’t love the sea, the burnt orange sunsets, the surprise visits from dolphins or the primal satisfaction I get from covering long distances by harnessing the power of the wind like a modern-day explorer with an espresso machine.

It’s just that I’d rather explore land.

And it’s not because I get seasick (if iron guts were the mark of someone destined for a life at sea, then I fit the bill) or because I long to have the stability of earth under my feet. It’s because I love to run long and far, bike up and down hills, clamber up mountain sides, ski down them, play soccer and go roller-skating; all things that I need vast swaths of solid ground for.

I thrive in places where I can lace up my sneakers, step out my front door and run as far as my legs will take me; where I can sweat out the day’s frustrations and run away with just my thoughts whenever I want to without having to bother with lowering the dinghy into the water, fixing the cumbersome outboard on the stern, refilling the gas tank and waiting impatiently for the crew of Cheeky Monkey to get ready to go to shore, too.

Our friend’s dog, Sophie, demonstrating the dinghy-waiting game

So when my feet finally touched land in Antigua, after 20 days of sailing across the Atlantic Ocean, I kissed the ground and grabbed my sneakers. I felt sure in that moment that nothing would make me happier than spending a good long chunk of time — a year, perhaps — in the Caribbean, where a mere day sail would drop me in another stunning anchorage off an island covered with trees and hills and roads where I could run and explore to my heart’s content. I was keen to spend less time at sea and more time running back and forth across the lush, green Virgin Islands, which I’d only become briefly acquainted with a year earlier, when we sailed through on our old boat, Hideaway.

The Caribbean is well-known as an aquamarine Mecca for long-term cruisers and vacationing boaters. The USVIs and the BVIs, especially, are famed for their consistent winds and the fact that all you need for “charts” is a hand-drawn map showing roughly where the land masses are. There’s no need for a depth sounder, though sailing in the Virgin Isles requires you to keep a vigilant lookout, not for the shallows you might hit, but for the novice “credit card captains” who may confidently cut you off or, worse, smack into you on an otherwise beautiful day in the busy cut of Sir Francis Drake’s Passage.

Once, we made the mistake of sailing Cheeky Monkey through the famous passage while flying “The Big Banana,” our spinnaker. We watched nervously as a chartered catamaran headed straight for our starboard hull with no one on deck or at the helm. As the boat approached quickly, Ryan hailed him on channel 16 with increasing anxiety in his voice.

“Tropical Island, Tropical Island, Tropical Island, this is sailing vessel Cheeky Monkey.”

No response.

“Tropical Island, Tropical Island, TROPICAL ISLAND!”

Still no response.



Plowing ahead on our fastest point of sail at a brisk 9 knots, we debated dropping the spinnaker and putting the engines on to steer away from a costly mishap, but in the time it took us to debate a course of action, we’d run out of time. So we blew our foghorn and Ryan and I began screaming in an attempt to wake up any sleeping or inebriated crew on the skipper-less boat.

A man and a woman with a baby on her hip eventually emerged on deck, at which point our screams grew louder with no effect on the charter boat’s course, which was now so close to us that I could have slapped the skipper upside the head from where I was standing on the bow.

Ryan was red in the face, bellowing about right-of-way and gesturing with his VHF radio as the man on the charter boat slowly walked to the helm without any show of alarm whatsoever. When he picked up the radio, the man simply said, “It is the rule that the boat on port tack must give way to the boat on starboard tack.” To which Ryan replied, “Yes, that is correct! And YOU are on a PORT tack! I am on a starboard tack! To clarify, as you seem to be confused, a port tack is when the wind is coming over the port side of the boat!” To which the man calmly replied, “That is not my understanding. I think you should consult your rule book again.” At which point Ryan wrapped the VHF radio cord around his neck and threw himself overboard. Well, not really. But that is what he looked like he might do.

But I digress. The risk of colliding with over-confident and under-skilled vacationing sailors in the Virgin Islands aside, there is a very good reason why so many boaters flock to the Caribbean in the winter to get a slice of the cruising life — the islands are stunning and not at all over-developed because most islands, with the exception of St. Thomas and other cruise ship ports like Sint Maarten, can’t be reached unless by boat. That, and the fact that you can sleep off the numerous coconut Painkillers you drank the night before, lazily raise your anchor sometime before noon, and reach yet another white-sand paradise in time to drop anchor and enjoy the sunset with a cocktail in hand, makes the Virgin Islands the go-to option for snowed-in sailors escaping the USA and Canada.

View of Maho Bay anchorage, St. John, from the top of a very steep hill

Plus, direct flights to St. Thomas and St. Maarten from New York meant if we stayed in the Caribbean for a year, friends could easily visit us from the States and, as an added bonus, we could spend more time with all our cruising friends who were semi-permanently based in the Caribbean, like Brittany and Scott (Windtraveler), Rebecca and Brian (Summertime Rolls), Genevieve and Eben (It’s a Necessity) and Peter and Jody (Where the Coconuts Grow). I say “semi-permanent” because cruisers are always on the move, but many of our boating friends have made the Caribbean their home for the foreseeable future.

But somehow, the next time I blinked, three months had flown by and we had spent most of our time anchored off some part of St. John or another. It seemed obscene to have spent so much time on just one island after we zipped so quickly from France to Spain to Ibiza, then across the Mediterranean twice (while also attempting to row a boat across the Med…twice), to a skimming stopover in Gibraltar, then on to Morocco, the Canary Islands and then across the Atlantic to Antigua, which meant we covered over 5,000 miles in the space of just five months. So how did we find ourselves spending 3 months on and around one Caribbean island?

The only way I can explain this is to describe what seems to happen to me after long bouts of moving fast and furiously. I suddenly get the urge to sit still for a while, develop a routine, wake up to a consistent view and get off the boat every day to exercise and explore. And, to me, St. John is the Goldilocks of the Caribbean islands — it’s not too remote (it has grocery stores, bars and restaurants) but it’s not too touristy either, since nearby St. Thomas is the sacrificial cruise ship port — plus, it is covered in well-maintained hiking trails that lead to the most beautiful and secluded beaches as well as untouched snorkeling spots.

Basically, after five months of constantly being on the move and always feeling like we were in a rush, it felt like a luxury to spend three months moving slowly from one anchorage on St. John to another, essentially oscillating between Maho Bay on the north side and Hansen Bay on the south side, depending on the direction of the swell.


You have to run uphill for quite a while to get this view of Hansen Bay

It’s the topography of St. John that drew me in and made me want to stay a while — the rolling hills, bleached white sand, palm trees and the stunning, idyllic bays that I could imagine being the backdrop for those widely shared zen-inspired quotes about life. But, more importantly, I’d heard about St. John’s 8 Tuff Miles, a race that runs every year from Cruz Bay to Coral Bay, along a road that soars up and down hills so brutal that cars struggle to make it to the top. It sounded exactly like what I needed after 20 days at sea with nowhere to run. And what better place to train for a run on St. John than the killer hills of St. John themselves?

So Ryan and I registered for the 8 Tuff Miles and began our training on the sharp hills winding up and down and around Hansen Bay, on the south side of St. John. We got into a routine of heart-attack-inducing hill sprints in the midday sun, starting “easy” with 4 miles of quad-burning uphill panting and, after a few weeks, worked our way up to 8 miles on the toughest inclines we could find, cursing every inch of the road and the masochist who thought this island was the perfect venue for a running race.

And then I met a die-hard local runner who told me about an inaugural 13.6-mile trail run on St. John just two days after the 8 Tuff Miles, which sounded strangely appealing after all the running I’d been deprived of on the Atlantic crossing. So I signed up for that, too. I offered to sign Ryan up, but the look he gave me after he finished the 8 Tuff Miles said he’d had enough near-heart-attacks for one week. Which left me and 33 other running fanatics to line up for an uphill half-marathon just two days after the brutal 8 Tuff Miles Race.

It turns out running every single trail on St. John from one end to the other is not only a great way to see the beauty and diverse geography of the entire island, but it’s the best way to gain an appreciation for just how many well-maintained trails the island has to offer. It’s a runner/hiker’s paradise, which makes it a paradise for Ryan as well, since he can just throw my running shoes at me when I’m getting irritable and send me off the boat to unleash some of my energy on 13.6 miles of trail options. Well, 13.6 if you have a good sense of direction. For the directionally challenged, like myself, it may or may not have taken 15.5 miles of running (off-trail, at times, as I followed creek beds I thought were trails) to get from one end of St. John to the other. Needless to say, I was in heaven.


1200 people turned up to run the 8 Tuff Miles on St. John

But this is where Ryan and I diverge in our traveling urges. I find a beautiful spot I can run around for a while and it makes me want to sit still and get to know the place. Ryan finds a beautiful spot (that he doesn’t mind running around for a while) and it makes him wonder what else is out there, either in the next harbor or across the next ocean.

Soon, after a few months of wearing down the trails of St. John and imbibing cocktails with friends at all our usual spots in the BVIs, I could see Ryan was getting the itch to move on again. So I took this as my cue to look up fitness options and hiking trails in the islands further south of us, as it seemed likely that we would work our way down to Grenada and spend a glorious hurricane season hanging out close to land. Perhaps I’d join the Hash House Harriers or the Crossfit gym in Grenada.

Except Ryan’s itchy feet seemed to be pulling him in a different direction altogether. He started mentioning with increased frequency the sailboats who were headed for the South Pacific as if he were summarizing newspaper headlines with a few not-so-subtle additions.

“Have you seen Starry Horizons is getting ready to go through the Panama Canal? Man, the Panama Canal…that’s going to be a blast, don’t you think?”

“Have you seen Vagabonde’s Facebook update today? They’re heading for the Galápagos. How incredible would it be to sail to the Galápagos?” (See what I mean about not-so-subtle?)

As time passed over me at a pleasantly slow pace in the Caribbean, for Ryan, the passing of time seemed to be driving him into an urgent frenzy. And the more Ryan excitedly mentioned what other boats were doing and where they were going, the more it became clear that Ryan’s itch would only be cured by following in their footsteps.

“We can sail the Caribbean any time in our lives,” Ryan argued. “But I don’t know if we’ll always be able to cross the Pacific. I think we should go for it.”

“But we just crossed an ocean,” I whined. “I like it here. I like running. I like getting off the boat.”


What’s not to like about this? (Maho Bay)

“You can do that in the South Pacific!” Ryan said. “I promise. You can go surfing. And wind-surfing. And kite-boarding. By all accounts, the islands in the South Pacific are just to-die-for.”

And so he persisted, despite my protests against being marooned on a boat for weeks on end with nowhere to run. As a tactic, I reminded Ryan of the torture that is being stuck on a boat with me going out of my mind from inactivity. Had he forgotten all those times I threatened to get my own boat or, at the very least, a hotel room on land? In a place far, far away from the boat? No, he hadn’t forgotten. But he would not be deterred. It only increased Ryan’s motivation to research the quickest route from the Galápagos to the South Pacific and then talk to me about it as if there were no concern whatsoever that I might kill him and throw him overboard two weeks out to sea.

But, given time to mourn my loss of endless running options, I started to come around to the idea of sailing across the Pacific. Involuntarily, I started to get excited about the idea of sailing up to sea lions and sea turtles and blue-footed boobies in the Galápagos and I started to dream of the postcard-perfect waters of the South Pacific and wonder what we might find there.

Because that’s how this boat life works for me. To me, a boat is an adventure-ship that allows me to pull my mobile home up to the most extraordinary places in the world, places I might never get to if I only traveled by plane or car, places that offer opportunities for exploration and learning that make the long, inescapable journeys at sea completely worth it. And, of course, there are the extraordinary experiences of the journeys across oceans themselves, which I wouldn’t trade for any stretch of land. Those experiences at sea, when we are forced to be completely self-sufficient, have become the Jenga blocks, stacked one on top of the other, that have formed my character and informed my self-confidence. Because there’s nothing like solving a problem, big or small, in the middle of the ocean or in the heart of a raging storm to test your inner strength and mental fortitude.

This is also how the push and pull of my and Ryan’s independent enthusiasms work to create the tumult that is our co-planning for the future. Ryan has a tendency to dream up insane plans, latch onto them, and introduce them like there really is no better option. To illustrate, here are a few quotes from past conversations:

“There’s a gala for the Tennis Open going on over there. Hey, look, there’s Jennifer Capriatti and Monica Seles! C’mon, let’s crash it.”

“I think I might take a job in Sudan for a few months so I can pay off my debts.”

“My school just shut down their teacher training center. I was thinking, what if we started a teacher training center?”

“I was thinking, we should buy a sailboat. Yes, I know we don’t know how to sail. But from what I’ve read, that’s not important. We can learn.”

“I’m tired of New York. We have a boat. I say we just sail out of here and see what happens. We can hire someone to run our businesses. How hard can it be?”

“I’ve just signed up to do the Clipper Round the World Yacht Race.”

“I have an idea. Let’s buy an old, beat-up car in England and drive it to South Africa. Oh, it takes eleven months? Scrap that. Let’s hire a car in Johannesburg and drive it to Cape Town.”

“I have an idea. Let’s rent a camper van and drive across Australia.”

“Eben and I have signed up for this race in Tanzania where we take a beat-up fishing boat with makeshift outriggers, a plywood rudder, a bamboo mast and a handkerchief for a sail and we sail it to Zanzibar.”

“Let’s sell the businesses and buy a bigger boat.”

“Let’s scrap the Caribbean and go straight for the South Pacific.”

Each of these conversation starters were met with my immediate skepticism (because someone has to think these things through, right?). But once the seed of Ryan’s idea was planted, it often started to take root and I found myself imagining the next place we might end up. And I felt a gurgle of excitement in my gut when I thought about what this next potential phase of adventure might offer in the way of new land to explore.

Sometimes I even found myself adding my own mad-cap schemes to the mix. Take, for example, these choice quotes:

“There’s a marathon coming up in two months. I’ve never run one, but I think we should do it.”

“I’m applying for a summer internship in Azerbaijan, Armenia and Georgia. It’s just for a month or two.”

“Let’s go to New York. I’ll get my Master’s degree and we’ll be out of there in two years, tops.”

“Property in New York City is outrageously expensive! Let’s buy a log cabin in a ski town instead.”

“I found this adult ski racing program I want to join.”

“Have you seen that movie Whip It? Well, there’s this roller derby team recruiting players…”

“I want to start a blog. Can you build me a website?”

“There’s an all-female rowing crew looking for someone to row across the Atlantic with them. It would take about 45 days. At least. No? Not a good idea?”

“There’s an all-female rowing crew looking for someone to row around the Isle of Wight with them. I volunteered.”

“There’s this rowing race across the Mediterranean…300 miles…”

Upon further reflection, perhaps it’s not just Ryan who pulls our plans in all kinds of crazy directions.

But I stand by my statement: I’m not a natural-born sailor.

I am a lifelong traveler and adventurer; someone who craves change — new experiences, new smells, new foods and new thrills — always. So sailing fits nicely alongside my own desires for travel and adventure. And once my momentary skepticism has passed and Ryan’s enthusiasm has won, I am always thrilled by the prospect of discovering yet another strange, new place in the world.

This process of navigating towards the future with Ryan has a kind of ebb and flow, like the sea — sometimes I find myself fighting the current to get where I want to go. But, sometimes, it occurs to me that maybe it’s better to just relax, go with the flow and see where the next wave takes me.

And it looks like this next wave is carrying me off to the South Pacific.



Sailing Across the Atlantic Ocean


On Birds and Boredom: Sailing Across the Atlantic Ocean post image

On the second day of our Atlantic crossing, a bird flew in through the porthole next to our bed in the owner’s cabin.

I was on night watch with Kristi when Ryan appeared in the saloon with a look of dazed confusion on his face.

“There’s a bird in my bedroom,” he mumbled.

I looked at Kristi and laughed, assuming Ryan had either just woken up from a vivid dream and hadn’t shaken off the sleep yet or he was sleep-walking around the boat talking nonsense. Either way, it was funny, which is why I couldn’t stop laughing as I asked Ryan to clarify. “What?”

“There’s a bird in my bedroom.”

Kristi and I looked at each other in disbelief as we made our way downstairs to the owner’s cabin to see what Ryan was talking about.

Sure enough, perched on the floor next to my bed, was a little black and white bird looking around and hopping lightly across the floor, not at all fazed by the two large humans bent over it, staring and giggling.

“Oh my God, there really IS a bird in the bedroom!” I said.

“I told you,” said Ryan, rubbing his eyes and yawning. “It flew past my head while I was sleeping and woke me up.”

“Aw, he’s so cute!” I said, slowly inching towards the bird. “What are you doing in here, little guy?” I cupped my hands softly around the little bird’s body, expecting it to struggle and fight to fly out of my grasp. But instead the bird sat calmly as I scooped it up and walked upstairs to the saloon.

The pumpkin seeds were of no interest to this bird (Photo by Kristi Wilson)

I set the bird down on our table outside, again expecting it to fly frantically around the cockpit, trying to escape, but it didn’t. The bird seemed tired, like maybe he got lost and had stopped to get some rest before continuing on towards its planned destination. I set a bowl of water and some sunflower seeds on the table, which the bird showed absolutely no interest in. But I didn’t want to be a bad host; I had to at least try to offer our little guest some refreshments.

The rest of my night watch passed without incident and though the sunrise was as pretty as any sunrise I’ve seen at sea, the sky streaked with shades of pink and purple, I don’t remember anything else about the day.

The sunsets are always stunning on the Atlantic Ocean, it seems (Photo by Kristi Wilson)

Which is pretty much like every day that passed on our Atlantic crossing. Days consisted of long stretches of doing nothing in various positions on the boat — at the helm, in the cockpit, on the beanbag chair on the foredeck, in the saloon, on the sun lounger next to the helm — name the space and you could usually find a half asleep crew member curled up there trying to pass the time reading a book, watching a movie, playing cards or just staring out at the waves.

The details of the long hours spent doing nothing have slipped from my mind like water through my fingers. But the animals we encountered became the hard, vivid memories that stood out when I thought back on each of the 20 days that passed as we bobbed around on the Atlantic Ocean. The bird that flew into my bedroom, all the fish we caught, the dolphins that played in our wake, the family of whales that circled our boat, the squid we found in our dinghy and the flying fish that threw themselves at the boat during night watches; those are the things I remember vividly about the crossing. My memories are marked by a string of animals on an ocean timeline.

Morgan proudly showing off his big catch

On every ocean crossing I’ve ever done (which is 3 now — twice across the Atlantic Ocean and once across the Southern Ocean), memories from the first few days seem to be lost to the walking dead that are the crew on board. As everyone adjusts to their strange sleep schedules, as well as the seasickness that usually strikes a sorry few of the crew, there is a lot of stumbling around silently and brewing strong coffees to shake off the malaise that has blanketed the entire boat.

For the first few days, the priority for crew is to keep the boat sailing, try to eat regular meals and stay awake for the few hours we’re on duty during the day. When we’re not on watch, we can all be found strewn around the boat in various states of sleep or almost-sleep, either clutching a book while curled up on the foredeck in the beanbag chair, stretched out on the settee half asleep hugging a laptop (that’s my usual position) or lying in bed trying to watch a movie.

If all of this sounds boring and rather uneventful, that’s because it is. And that’s exactly why I wasn’t at all worried about the idea of crossing the vast Atlantic Ocean on our own boat — after all, I’d already done it on the Clipper Race, and we didn’t have the luxury then of turning on our engines when the wind died. On the Clipper Race, we sat flailing around in the Doldrums with our sails hanging limply for 10 days, baking in the sun and going out of our minds with boredom.

There’s nothing more boring than having no wind on an ocean race

So when Ryan and I were given the option of having our new boat, Cheeky Monkey, delivered to the U.S. from France for a hefty fee of $15,000, I barely paused before stating we would pick up our boat in France and sail it across the Atlantic ourselves.

Which is kind of crazy, now that I think about it, because I can vividly remember the thrilling terror I felt in December 2012 when we set out on Hideaway to sail from Fort Lauderdale to Bimini, Bahamas. I was imagining all the things that could go wrong as we lost sight of land and were out of range of other boaters, considering we barely knew what we were doing as sailors and had never done a landfall like that before. And that was only a thirty-five hour sail I had gotten myself all worked up over.

Of course, things did go wrong, as they always do. Our engine started over-heating and spitting sea water out onto our cabin floor, which turned out to be the result of a corroded heat exchanger. But by the time we reached Bimini with our faulty engine, we had stretched ourselves, mentally and physically, beyond the range of what we thought we could do. And it made us wonder what would happen if we continued to go further.

Looking back on our learning days on Hideaway, I am awed by this newfound fearless determination I have to cross oceans, which I know was not something I even remotely desired to do before meeting Ryan, and it certainly was not an idea I felt at all comfortable with even 5 years into sailing Hideaway around the harbors of New York.

So I understand when I meet sailors and cruisers out on the water who never aim to sail beyond the Caribbean, or maybe even their home ports. They name the discomforts of being at sea for extended periods of time and how they prefer to avoid all that. Sailing is something they experience for fun — the increased risk of being far from land and support is something that overshadows any idea of fun in sailing away from local shores. I absolutely understand all of those sentiments.

But somehow, I have found myself over the years stretching just a little further than I did before and exercising the muscle that dreams of places even further away until I’ve found myself feeling more and more comfortable being out of sight of land and growing more confident in my boat and my own sailing skills.

5 years ago, if you asked me to do this, I’d be saying “HELL NO.” (Photo by Kristi Wilson)

To look back on where I began is always amusing because I have just described a 20-day Atlantic crossing as being, essentially, boring, but for the string of animals that sent me shrieking and running periodically across the foredeck to have a closer look at what was splashing on the surface. The moments that filled the spaces between those animals I can’t recall without yawning, as they were pleasantly dull moments full of silence, lapping waves, a few meals and numerous books.

The bird that flew in through our window on the second day of our Atlantic crossing hopped around our saloon and cockpit for the entire night, seemingly comfortable in the presence of humans, every now and then sitting still and dozing off. It made no attempt to fly off into the darkness and we continued sailing on course with our little bird guest on board, wondering how long it would stay. It was as if the bird had flown beyond its capacity and got lost in the dark, but had the good fortune of finding a friendly boat where he could sit down and rest for a bit while figuring out what to do next.

I hope Cheeky Monkey can be hospitable to all lost birds on the ocean

At the crack of dawn, as the sun crept up over the horizon, the bird perked up and looked beyond the cockpit towards the sky. And without warning, the bird flapped its wings and flew off toward some unknown destination which maybe, after some rest, seemed possible to reach after all.

Like that little bird, we had sailed out into the unknown many times and encountered problems that meant we had to stop and regroup before continuing onwards. But with every obstacle we overcame, we found a boost in confidence and an increase in curiosity, wondering how far we could go the next time.

Which is why crossing the Atlantic Ocean on Cheeky Monkey isn’t the only milestone I feel I’ve reached in my sailing experience. It’s that I find myself describing an ocean crossing as “mostly boring” with the exception of the animals that punctuate the days, illustrating how far and wide my comfort zone has stretched since the early days of sailing Hideaway.

It’s taken many years of lots of little leaps, along with a fair bit of rest and regrouping between journeys, but it finally feels like our wings are at our strongest and there is nowhere we can’t fly to. Which begs the question, where shall we go next?

It may be boring at times to cross oceans, but it sure is beautiful


Update from Tasha

Hey everyone! If you haven’t yet watched all 4 of our videos about crossing the Atlantic Ocean on our YouTube Channel, check them out! It was an epic adventure.


Video links

There’s this one — Atlantic Crossing: ARE WE READY?


And then there’s this one — Sailing the Atlantic: SHE WENT OVERBOARD!


And then there’s the one in which we were becalmed for 4 days — Atlantic Crossing: STUCK IN A WIND HOLE


And, finally, this one, in which we are ecstatic to have finally reached land — Atlantic Crossing: WE MADE IT!


I’ve been thinking a lot about our Atlantic crossing because we are soon embarking on our journey across the Pacific Ocean and I’m hoping we’ll have learned from our mistakes on the Atlantic and have an even better adventure on the Pacific! We’ll see!


5 Lessons in Outfitting a New Boat


I’ve mentioned before, in a post called The 80% Rule, that buying a new boat is not at all like buying a new car, unless you expect your new car to be delivered with a missing stereo, a broken speedometer and a bumper that falls off as you pull out of the dealership.

The problem is there are so many parties involved in creating the finished product that is your brand-new boat that the quality varies between different components of your vessel, depending on the responsibility assumed by the manufacturer (in our case, Fountaine-Pajot), the broker, the post-factory outfitter and the various companies who provide warranties for the products you’ve selected.

And though you may think that all these parties are working together towards the common goal of providing you with a fully working boat outfitted with all the gadgets and gizmos your heart desires and your wallet can afford, the truth is there are differences in how each of these parties approaches that goal while also catering to their bottom line.

This list of lessons learned comes directly from our experience working with Fountaine-Pajot, our broker, our post-factory outfitter and the various companies who sold us products that we researched and chose for our Helia.

Of course, every new boat owner will have a different tale to tell about their buying experience. So keep in mind that the advice listed here is nowhere near comprehensive and should be taken as a pinch of salt in a mixed stew of experiences. Nevertheless, these are the true stories behind the lessons we’ve learned.


This is a Helia in the process of being built

Lesson #1: If it can be installed by the factory, get it installed by the factory.

I can’t speak for all yacht manufacturers, but my hunch is that this rule applies to most, if not all boat brands. In our experience, Fountaine-Pajot ranks at the top of the accountability list for any and all products they install. After all, it is their name branded on the side of the boat; not the broker’s name or the outfitter installing your various gadgets.

And let me be the first to say that the overall quality of the work done by Fountaine-Pajot was top-notch. And, more importantly, when things went wrong (as they always do with a boat, whether it’s old or new), FP took care of the repairs, replacements and labor immediately, no matter where we were in the world. For example, we had an issue with a terrible creaking sound in the hull, which seemed to be coming from our port stern when underway. FP identified it as a problem they had seen where the window wasn’t bedded properly in the fiberglass, causing friction, so they immediately over-nighted a new window to Menorca and paid for it to be replaced and reinstalled properly. The service was prompt, thorough and we never touched the bill.

One thing we’ve learned is for big installations like the generator, water-maker and air-conditioners, there is so much crucial wiring involved that it is best to have these items installed by the factory while the hull is in the process of being built, not after the boat is a finished product.

Luckily for us, our generator, water-maker and air-conditioners were installed by Fountaine-Pajot. But the list of installations that ended up being commissioned by our post-factory outfitter was not discussed with us, and if we’d known then what we know now, we would have specified what the factory should install; in short, everything that the factory was offering to install. And we would have done our own research into who should install the items not installed by the factory.

Take the ice-maker, for example. As we ordered our boat from FP, through an FP dealer, it never occurred to us that it wouldn’t be installed by FP. But the job of installing our ice-maker was given to our post-factory outfitter. Which meant that when the ice-maker was delivered broken, installed broken and never worked, there was a lot of shrugging, scratching of heads and not responding to emails requesting a new ice-maker.

We thought about selling the ice-maker for scrap metal or turning it into a spare anchor, but really all we wanted was for our outfitter to take responsibility for a broken item they installed. But, as the post-factory outfitters are at the bottom of the list of parties that maintain accountability for their products, we still don’t have a working ice-maker.


lessons-outfitting-new-boat-turf-to-surf-sailing blog

No amount of glaring at this ice-maker is going to bring it to life

If FP had installed an ice-maker that didn’t work, they would have immediately shipped us a new machine and paid for the installation. It would have been a no-hassle request and, most likely, we would have had a working ice-maker within a month.

In the end, after eight months of battling with the outfitters to take responsibility for a faulty product they installed, we eventually gave up and took a refund from our broker for the ice-maker. But I’d trade that cash in any day for a working ice-maker and all the lost hours spent sending emails that resulted in no change in the state of our ice-maker.

And whilst I have no doubt that the first G&Ts we pour over ice from our future working ice-maker will taste all the better for having to wait; lets face it, eight months is a pretty long time to be drinking warm gin.


Lesson #2: Buy specialty products from an authorized dealer (or direct from the manufacturer).

Being the fast-walking, coffee-guzzling, appointment-juggling, I’ll-pay-more-if-it-saves-me-time kind of New Yorker that I am, I appreciate a one-stop-shop opportunity when I see one.

By the time we got to La Rochelle, France last summer, I had a growing list of overwhelming jobs on my plate, in addition to the fact that we’d taken on the colossal task of launching, outfitting and stocking Cheeky Monkey for her round-the-world voyage in just over a month. So when the outfitter our broker hired offered to order everything we’d scribbled on our growing list of necessities, we snapped up the chance to hand over the logistical burden.

sailing blog turf to surf
Schlepping and organizing is not my idea of fun

And maybe it’s possible that, somewhere out there, at the end of a rainbow, there is a pot of gold and a perfect outfitter who can act as your one-stop shop for every piece of boat equipment you need. In my dreams, this outfitter would save me all the miles spent driving around looking for dealers and the endless phone calls to customs offices to track down packages. In my dreams, everything would be magically delivered to my boat with valid warranties and legit registration papers.

As you might have guessed from the direction this thread is taking, however, that didn’t happen.

And this is where I bring up the sore subject of our autopilot.

(Note: If you ever run into me at the bar and want to see my blood pressure go from zero to sixty in under a second, just mention either the autopilot or the ice-maker. Or, better yet, just buy me a drink and don’t ask about the autopilot.)

I mean, how could we be on a new boat and not have a working autopilot, you ask?

That’s a very good question with a two-part answer:

We are somewhat to blame for our stubborn choice of brand because we decided to go for Garmin based purely on the hell we went through with a Raymarine autopilot on Hideaway, our old boat.

But in hindsight, that is kind of like deciding you could never date another Brit because your last British boyfriend cheated on you. Maybe it wasn’t British men? Maybe it was just that one autopilot?

You get what I mean…and what I mean is, all my research says Raymarine has one of the best cruising autopilots on the market right now, and we ignored all that info because of a bad experience we once had with Raymarine. It was like we’d torched all our ex’s photos and told our friends never to utter the name “Raymarine” in our presence.

But, the fact is, we chose a brand for a reason – albeit a bad one – and we had every right as owners to install whatever brand autopilot we wanted. It’s just unfortunate that we went with Garmin because the outfitter our broker hired to install our Garmin turned out NOT to be an authorized Garmin dealer. In other words, there was an authorized Garmin dealer in La Rochelle, but that wasn’t the company our broker hired – in short, he hired the same outfitter who burned us on the ice-maker. And I’m sure you can imagine how that story ended.

So take this as a cautionary tale and know what happens in this situation: if your broker hires a non-authorized dealer to install your electronics, then any warranty for the installation of that product is null and void. And if your broker fails to take responsibility for that mistake while your outfitter completely and utterly screws up the installation to the point where your autopilot will do nothing but drive like your drunken British ex towards a crash jibe (which is what happens when the wiring is all wrong and the compass is installed on top of the engine), then you are not only left with a mixed metaphor, but you’re stuck with a broken electronic system you paid tens of thousands of dollars for and a bill for repairs which the manufacturer will not cover. How’s that for an expensive lesson?

Which provides a nice segue to the next lesson about the marine industry in general…


sailing around the world blog turf to surf

It’s so stressful telling this story that I am taking this moment to highlight a major success: buying this bean bag chair

Lesson #3: Expect to spend a lot of time babysitting marine workers…unless you’re okay with random holes being drilled all over your boat.

Remember how I said buying a new boat is nothing like buying a new car? Well, imagine if you brought your brand-new Mercedes into the shop because you wanted to upgrade your stereo to a state-of-the-art Bose system for the sole purpose of rocking out to high-quality tunes on your morning commute to work.

And imagine you assumed – as you do – that the shop guys have read the installation instructions and know where a car stereo goes. But when you show up a week later to pick up your new car, excited to blast the new speakers in your kick-ass stereo, you find the stereo isn’t on the center console, where you expected it to be. Instead, there is a hole in the glove box where the mechanics have randomly shoved the stereo and glued it down with silicone. And you’re standing there with your head in your hands saying, “Why in the hell did you cut a hole in my glove box?!”

Meanwhile, the mechanics are shrugging their shoulders saying, “Well, you never said we couldn’t put the stereo in the glove box. I mean, if you want us to move it, we can…we’ll just tape over the hole and put some vinyl spray on it…no biggie. Or you can pay for a new glove box.”

Which is when your head starts fermenting like an overripe tomato from the blood pressure building up in your neck, and your broker calls an ambulance because he thinks either you’re having a heart attack or, judging from the crazed look in your eye, he might be the one who ends up in the hospital.

This is pretty much what happened to us every day for a month on our brand-new boat in La Rochelle. We would wake up in the morning with our blood pressure really low, thinking “Today, we will manage things better and we will preempt the stupid places people might cut holes in our hull.”

And every day, we discovered new ways to define “stupid.”

Because here’s the thing — we were physically on our boat, available for consultation every single day, and any time we turned our backs, we’d discover another hole being drilled where it didn’t belong, in a completely different spot from where an installation was meant to happen. If I had a dollar for every time I heard Ryan scream over the din of power tools, “What are you doing? That doesn’t go there!” we might have enough money to pay for a new autopilot.

And while you have very little ability to influence the work force at a boat factory like Fountaine-Pajot, you should be able to control any post-factory work that is being done on your boat once it’s left the factory. I know, I know, you have better things to do than to babysit – and these guys are paid professionals, right? So you should just be able to leave the boat and go run all the errands that are piling up on your plate and let them handle the jobs you’ve given them, right?

Wrong. You hope that the guys working on your boat are 100% professional and none of them are high school kids who just learned how to wire an autopilot by watching a YouTube video, ignoring all the instructions that essentially say “DON’T INSTALL THE COMPASS NEAR A BIG HUNK OF METAL…AND, YES, THE ENGINE IS A BIG HUNK OF METAL”  But our experience tells us that you can’t leave your boat when work is going on. And you can’t trust that the workers on your boat know what they’re doing 100% because you don’t know who is the expert and who’s on their first-ever boat job until you’ve spent some time watching them work.

Which leads me to the next lesson we learned long ago from being burned by the marine industry in different parts of the world…

 broken autopilot cheeky monkey
When Ryan was told the autopilot was working – such false hope in this photo

Lesson #4: Never pay for everything up front and always withhold your last installment until the job is done and you have what you paid for in hand.

We live in a world where we want to trust everyone to do the right thing. But the truth is, life gets in the way, other jobs come up, personal problems arise or, in the worst-case scenario, you’re dealing with an unscrupulous person or company. And when that happens, the only tool you have for negotiating with someone who is failing to finish the work you hired them to do, is money.

When we sailed out of La Rochelle in August 2015, we still owed the outfitter one final payment of $4,000, pending two items that still needed to be resolved – our broken ice-maker and the missing registration papers for our new AB dinghy and Yamaha outboard.


We were like kids at Christmas when our new dinghy arrived

After weeks of pestering the outfitter for the official registration papers, he eventually responded that he didn’t have them and said, briefly, “You don’t need them.”

Which, of course, is ridiculous. What does he mean, we don’t need proof of ownership for a brand-new dinghy and motor we’ll be driving through harbors all over the world? If we ever bring our boat to the U.S., we will be required to register Bananas, our dinghy, with the DMV. And we can’t do this without official registration papers.

A back and forth ensued with the outfitter for months over this issue, frustrating us to no end, so that by the time we got to Menorca, we decided to visit the Yamaha dealer in Mahon to ask what paperwork they provide to customers when they buy a new dinghy or outboard. The Yamaha dealer graciously showed us the official registration papers, so we sent copies to the outfitter, demanding we get the same for our dinghy and outboard.

This is where the story takes a strange turn. After weeks of saying he didn’t have our registration papers, eventually we received email attachments of scanned documents that looked similar to the registration copies we’d sent them as an example. So we said, “Great! Send us the originals.”

To which the outfitter refused. He would only offer us his newly “found” scans, but not the originals, even though we were clear that we wouldn’t be able to register the dinghy with a scan of the document and that we now had serious concerns about how these “copies” suddenly materialized.

So again, Ryan wrote back insisting we get the correct, original paperwork. To which the outfitter replied he would do nothing more until we paid him the last $4,000 we owed for outstanding work.

As far as we could work out, the fact that the reason kept changing for why these registration papers couldn’t be produced could only mean one of two things:

1) Our outfitter accidentally scribbled his Swiss bank account numbers on the back of our registration papers, and so he worried if he handed over our papers, we’d steal his entire fortune.


2) The real registration papers never existed.

As per Lesson #2, if we’d gone to an AB or Yamaha dealer for our outboard and dinghy, we would have found ourselves in this situation.


Seriously, this is our dream dinghy – 25 HP!

In the end, the $4,000 we withheld was the only reason, after eight months, that we got our registration papers in hand. But even the $4,000 wasn’t motivation enough for the outfitter to do the right thing on his own. It took our broker’s involvement to track down the paperwork from AB and Yamaha and, once that was done, we transferred the money we owed. But not a second sooner.

What we didn’t get to withhold, however, was compensation for the lost hours spent badgering our broker and outfitter for eight months to deal with this unreasonable problem.

We also weren’t compensated for the stress of spending our life’s savings on a boat only to get an email like this from our outfitter:

“As you know I am a fighter, I promises you that I shall release nothing…I guess that you didn’t know that I work since many years with the D.O.D. (Division des Operations Douanières). They are very efficient all around the world, so don’t be surprise if, one day, you will have your boat under seizure by the local Customs.”

Yep. That’s the stuff of regrets. When you spend your hard-earned money on a dream and you find yourself being threatened.


Lesson #5: Reach out to other boat owners and get reviews on the outfitters who will be doing your post-factory work.

Ryan talked to a number of Helia owners (a big thank-you to Amy and David of Out Chasing Stars) to gain insight into the process of buying a new boat and working with a broker. It helped immensely in areas we knew to look out for, but obviously it didn’t prevent us from making all the mistakes I’ve named in the previous lessons. But the more insight, the better — it will give you a leg up in negotiating with your broker and avoiding some of the mistakes we’ve made in the process of buying our boat.

The truth is we love our boat and wouldn’t trade it for any other boat on the market. But the strife we went through to get the boat we love could have been avoided.


We may not need an ice-maker, but what I definitely don’t need is this hole

With the myriad forums available on Facebook, Reddit and boating-specific sites like CruisersForum.com, all it takes is one question posted online during your coffee break and a twenty-minute pause before dozens of messages will pour in, answering your questions about the quality of marine work in ports all over the world. And with the overflowing number of sailing blogs on the internet, you’re bound to find a blogger sailing on just the boat you want to buy.

Most likely, your broker won’t be forthcoming about bad customer reviews of your outfitter because he doesn’t want you to have any doubts about buying your new boat from him/her. But you can do your research and contact customers directly for their stories before you make your decision about who should do the work you need on your boat. At the end of the day, it is your hard-earned money, your time and your dream that’s on the line.

We’ve learned the hard way that the realization of a dream can be smooth or torturous, depending on who you work with.

I feel like there’s a public service announcement in all this: Don’t be a Cheeky Monkey. Have your ice and registration papers, too.

sailing-blog-cheeky-monkey-lessons-outfitting-new-boatIf only we knew then what we know now


Update from Tasha

Hey everyone!

I am always happy to answer questions about our buying experience. We are incredibly happy boat owners, even after all the teething problems we’ve had with the post-factory work and we’re very open to helping people have a better buying experience than we had.

You may have seen an earlier version of this post — sorry about that! I had to pull the post for some edits, which took some time as I didn’t want to say anything inaccurate. So I apologize if you’re reading this again.

I also want to say thank-you for reading and returning to this blog time and again to wonder when in the hell I’m planning to get my blog updated to current – soon! I’ve been working hard in my sunny office here in Panama, tapping away on my computer in an effort to get you more stories.



Questions from My Mom about Life on a Boat

questions from my mom about life on a boat

My Facebook Page can be confusing, I know. One minute I’m showing pictures of me lounging in a hammock on a Caribbean beach and, a few hours later, I’m posting an update of me eating sushi in New York City with friends I made during the Clipper Round the World Race…for example.

Even I find it hard to keep track of where I am on my blog, on my Facebook page and on my videos, let alone where I am in real life. Which is why I should be sympathetic when I call my mother and she asks questions like, “Where have you been for the last month?”

“Crossing the Atlantic, Ma.”

“Oh, so where are you now?”

“The Caribbean.”

“Oh, so you’re back in the U.S., that’s wonderful!”

“No, not exactly…”

I am nowhere near the U.S. right now, but I have been back to New York to see my mom three times since I sailed to the Caribbean. And each time, she has told me how grateful she is for my YouTube videos because now she can see for herself what I do with my days now that I no longer have a job.

(I don’t have the heart to tell my mother I don’t make the videos for her alone – though I’m grateful they help her understand my crazy life a little more.)

questions from my mom about life on a boat turf to surf

This is what my mother feeds me — I should really visit more often.

The truth is my mother doesn’t care why I create videos for YouTube; she’s just excited she can watch them and show me all the adventures I’ve been having every time I visit her. Yes, you read that correctly – my mom loves to play my videos on her television for me so I can watch the things I’ve done…and made videos of.

It’s kind of cute, actually – it’s like she uses YouTube as a way of connecting with me and showing me all the amazing stuff she loves about the internet…which is basically cats and watching me sail around the world. It would be like J.K. Rowling’s mother insisting on reading aloud all her favorite Harry Potter passages every time she met up with J.K for brunch. Not that I am comparing myself to J.K. Rowling – but you get the idea. It’s weird and adorable.

I should mention here that my mother is Korean and English isn’t her first language so, at times, reading all the words I post here on my blog can be tedious for her.

“Thank God for YouTube!” my mother says when she watches Chase the Story. “It makes me feel like I’m right next to you!”

It’s cute how she has taken on the mission of watching and sharing everything I create on YouTube. That is, until I, personally, am sitting in my mother’s living room, working away on editing a video, and I look up to see my mom is broadcasting a video I made on her Chrome Cast.

“Have you seen this one? With the dolphins?!” She exclaims.

“Yes, mom. I have seen it. I was there. I made it.”

This is adorable of course, but the reality is that my mom is seeing an opportunity to showcase my work to me AND interrupt me every 30 seconds to ask me what is happening on the screen at any given time. It’s both endearing and irritating.

And since I don’t have the wherewithal to video record my mother watching my own YouTube videos while asking me questions about what is happening in my videos, I thought I would share some of the gems my mother is throwing at me while I’m trying to do work in her living room.

  • You don’t actually use those things, do you? (Referring to the sails)
  • You can’t steer when you’re sailing, can you?
  • What kind of fish is that? Mahi Mahi? How do you spell that? (Looks up in Korean dictionary) Do you have another name? It’s not in my dictionary.
  • Can you eat that fish?
  • WOW, YOU MADE THAT DINNER?! (Referring to footage of us eating in a restaurant. I had to point out that we were not on the boat.)
  • What is that you’re pulling on, does that help you sail? (Referring to footage of me reeling in a fish — I had to point out that this particular activity has nothing to do with sailing).
  • How did you get that picture of the dolphins under water?
  • Why is Ryan afraid of horses?
  • How do you know these people on your boat?
  • Who is that girl?
  • Why does that guy talk funny? (Referring to our French crew’s accent).
  • Did the bird eat anything?
  • That doesn’t look hard. Is he stupid? (Referring to a crew member’s efforts to learn to tie a knot.)
  • Can you sail at night?

In light of the fact that I can get nothing done with my mother in the room, I have started to think about the concept of AMA (Ask Me Anything) and wondered if any of you out there might also have questions about my life at sea – what it entails, how we eat, where we go to the bathroom (a common question from children under five) and the complications we experience.

So let this be an opportunity for my mother to open up the table to questions from anyone about how we live our lives at sea and what it is we do with all our time as we sail around the world.

I will be on the move (as usual) for the next few days, but I’d love to read and answer your questions – post your thoughts in the comments below and I’ll do my best to answer!

And, mom, try to not to overload the comments section here…I know it’s hard. So many questions 😉





5 Lessons Learned from Managing a Crew

5 lessons in managing a crew sailing blog

When Cheeky Monkey reached the Canary Islands after five days at sea, it was clear the crew needed a stiff drink and some space.

This was our “shakedown,” our test run for the Atlantic crossing with our full crew of six: Meg and Kristi, our friends from the ’13-14 Clipper Round the World Race, Morgan, a French solo sailor we met sailing in the Bahamas, and Xavier, a close friend of Morgan’s who briefly sailed with him in the Caribbean. Our crew didn’t all know each other, as Ryan and I were the only common denominators, but we were excited for them all to get to know each other during our passage to the Canary Islands.

When we hit the fuel dock in Las Palmas de Gran Canaria on Kristi’s 29th birthday, we popped open a bottle of champagne not just to celebrate, but to let off some of the steam that had been building over the last five days at sea. For better or for worse, alcohol tends to act as a release valve for pressurized circumstances on a boat; it lubricates the tongue so that all the blocked-up grievances of the last few days and weeks come gushing out, filling the awkward spaces between crew. Which is exactly what happened on our first night out in Las Palmas.

If I ever thought introducing friends from different parts of my life was tricky on land, inviting virtual strangers to live together on a boat for a month as we crossed the Atlantic Ocean had the dramatic weight of launching a reality TV show.

sailing blog 5 lessons in managing a crew

In the Canary Islands: Ryan, Xavier, Tasha, Meg, Kristi (holding camera), Morgan

I watched as the drinking progressed and crew started to let loose some of the complaints they had about how the last five days at sea went, making it clear we would need to amend some of the rules and schedules Ryan and I had established at the start of this trip.

In our former lives, before we sold everything in 2015, Ryan and I were the bosses of a series of successful schools that we built from a seed of $800 and grew into a multi-million-dollar enterprise that succeeded in large part because of the talented people we’d hired and motivated to turn our educational and entrepreneurial visions into a reality.

And now it suddenly dawned on me that running a boat is very similar to running a company – in essence, someone needs to act as the head to establish the vision, the direction and the short-term goals that lead to the fruition of the big picture, the dream. In the case of a company, that dream might be to expand its operations across the country. Or, in sailing, it might be to cross an ocean, win a race, or circumnavigate the world.

But what if you found yourself in charge of a group of close friends? How do you manage people who aren’t your employees? How do you act as the head of a vision without acting as a “boss” to your friends? These were questions we asked ourselves when we finally got to the Canary Islands because, clearly, there were a few things we screwed up on that passage from Morocco.

It took some experimentation and a little hindsight to work out our successes and our mistakes managing a crew of friends for the first time, but here’s a little insight into what we learned on that first passage…

sailing around the world 5 lessons in managing a crew

Top-of-mast view of Cheeky Monkey in the Canary Islands

1. Crew happiness hinges on crew expectations…

…And it’s your job as Captain to manage those expectations. If you tell your crew they’ll have a private cabin to themselves and you stick them with a roommate when they arrive, they’ll be upset no matter how luxurious the room is you give them. If you tell your crew they may have to sleep in the cockpit and, when they turn up, they have a queen-sized bed to snuggle up in, they’ll naturally be thrilled.

That’s how expectations work – if you are transparent about the cons, people are often pleasantly surprised by the pros.

A few of our crew, having only experienced sailing in the Clipper Race on board 70-foot ocean racing yachts with no comforts to speak of, were thrilled to find themselves on board Cheeky Monkey with queen-sized beds, en suite heads and an espresso machine. They were used to long, 4 to 6-week passages while crammed into a smelly boat full of 20 crew whose personal hygiene depended solely on the regular use of baby wipes.

Being a solo sailor, however, makes it tougher to adjust to a boat full of people. It’s nothing like having an entire boat to yourself, enjoying long watches in solitude and setting your own schedules. Coming on board Cheeky Monkey to find watch schedules were drawn randomly out of a hat and that we banned alcohol consumption during passages was a surprise to some of the crew — this was not the carefree cruise with friends they were expecting. And though Ryan and I like our drink, we have always done dry passages because we don’t feel comfortable drinking at sea in unknown territories, so we never considered this rule would cause issues on board.

So what did we learn from our mistake? We need to be explicit about what the crew can expect in terms of accommodation, jobs and rules on board Cheeky Monkey before they get anywhere near the boat. If our crew have time to mentally prepare for what to expect on board, they’re more likely to be happy with their circumstances when they arrive.

5 lessons in managing a crew sailing around the world

The girls on Cheeky Monkey are happiest when there’s good WiFi 🙂

2. The skipper is the boss of the boat…

…Which is harder to establish on a boat full of friends rather than paid crew.

On Cheeky Monkey, the boss is Ryan and that’s because it’s our boat, our responsibility and, between me and Ryan, Ryan has the most experience as skipper. Ultimately, everyone should feel responsible for the safety of the boat, the crew and its equipment, but no one feels the weight of responsibility as heavily as the person who owns the boat.

When we set strict parameters for when to reef or drop a sail, it’s because Ryan and I know how much it costs if we damage the sails, the boat or any of our equipment. The Parasailor, for instance, is a $13,000.00 spinnaker. To rip the spinnaker because we didn’t drop it early enough would be a mistake that would tear a hole in our pockets alone, not the pockets of the crew on board.

Even if crew feel they have more than enough sailing experience to do maneuvers on their own, Ryan often insists that he be woken up for any change in direction, sails, etc. It may seem excessive or unnecessary, or even a bit too bossy for our sailing friends on board, but ultimately we are the ones who are responsible for the boat, the equipment and the safety of the crew.

So, in this case, being bossy is an unfortunate necessity.

 5 lessons in managing a crew sailingRyan has the tough job of being a manager to his friends

3. Being too relaxed causes stress.

That sounds like a contradiction, but when it comes to rules and schedules on board a boat, it’s true. When we set out from the Canary Islands, everyone drew their watch schedules out of a hat. If you got the crappy 2 am – 4 am watch, that was life. Drawing out of a hat was the only fair way to distribute the good and bad watches.

When we established the meal schedule on board, however, we weren’t strict at all about who did what and when. We stated that everyone was on their own for breakfast, but lunch would be served between 12 – 1 pm and dinner would be served between 6 – 7 pm. And the rule for clean-up was if you made a meal, you didn’t have to clean up from the meal. And we figured people would just rotate the responsibility of cooking lunch and dinner as they felt appropriate.

It seemed like an easy enough thing to do with six people on board — to share out the cooking — leaving plenty of time for me to read, write and sunbathe.

But what actually happened was that meal times had a kind of halo of stress hovering over them, as I never knew for sure whether I was off the hook or on the hook to cook a meal on any given day. So, as lunch or dinner would approach, I would find myself unable to focus on whatever I was doing because I’d be preoccupied with a kind of internal monologue. “Who’s cooking today? Is it my turn? No, wait, I cooked lunch yesterday, so it’s someone else’s turn. But it’s noon…has anyone decided what to cook? If I made lunch now, then I’m definitely off the hook for dinner. Should I just make lunch now?”

And then, after an hour of having this mental conversation with myself, usually Meg or Kristi would step up to the plate and save us all from having to think about making a meal. Which would make me feel guilty because it seemed like Meg and Kristi were cooking the majority of the meals.

So it wasn’t the cooking that was cutting into my guilt-free alone-time, it was the process of thinking about cooking that was interfering with all the things I’d rather be doing. Not to mention, it didn’t seem like the meal rotation wasn’t being shared out fairly and equally.

We fixed that problem in the last few days of the passage by simply assigning lunch and dinner duties to crew according to a schedule and implementing the rule that whoever was assigned to cook the next meal would do the washing up for the meal before it. It was simple, it worked, and it stopped the pointless conversations in my head for hours each day about whether I should or shouldn’t get up and make a meal for everyone.

My free time returned to its blissful, guilt-free state because I knew exactly when I was on the hook.

sailing 5 lessons in managing a crew sailing blog

As you can see, it’s a big job to feed 6 people on board Cheeky Monkey

4. Even experienced crew need training.

The first few days of our passage with crew, we pulled Ryan out of the watch rotation and had him be a “roamer.” The idea was that he should be woken up any time there was a question about whether wind speeds were picking up, whether we should reef or change a sail or whether we should be worried about a boat on the horizon.

It also meant Ryan could wake up periodically to check on crew at the helm during night watch to make sure they were following safety procedures (like having a personal AIS clipped onto them) and not falling asleep on their watch. This was as much to instill confidence in the skipper that the crew could handle their responsibilities as it was to make sure the crew got to learn all the maneuvers on board, like sail changes, reefing, tacking, jibing, etc.

Having the skipper be well-rested so he can spend ample time training crew is a crucial process that we go through with any new crew on board and it’s worked well for us so far. As in, we haven’t sunk the boat or lost any crew overboard as of yet. Success!

 parasailor 5 lessons in managing a crew
The Parasailor is an amazing sail, but it’s not cheap — it requires TLC and crew training

5. Put as many procedures / rules in writing as possible.

There are things we’ve gotten used to on board Cheeky Monkey that we don’t even think about and, therefore, we find it hard to remember what to tell new crew members when they come on board for the first time.

We have a written “departure checklist” in the front cover of our logbook so anyone on board can run through the list and make sure we’ve done all the engine checks and various items needed before we leave port.

We’ve also now written out our safety protocols, in addition to talking our crew through them, and posted them in the galley so crew can refresh their memory on where the EPIRB and fire extinguishers are located and what to do in the event of a man overboard.

One item we consult daily is the reefing chart for our sails, which came with our boat. Having absorbed all the disaster stories about catamarans being dismasted in high winds, I take our reefing chart very seriously and talk it through with the crew so they know how important it is to reef early. Having a written list of apparent wind thresholds just makes it easy to know when to reef without having to think about it too much.

sailing blog 5 lessons in managing a crew

The happy crew of Cheeky Monkey

All in all, our crew shakedown from Morocco to the Canary Islands went well. Despite a few arguments and tears in the bar when we arrived, everyone on board seemed to get along well and understand what their roles on board were.

Our French crew got over the alcohol ban and we allowed them to bring several bottles of Pastis on board for the Atlantic Crossing, and we stocked up on wine and rum, so long as the crew promised not to drink while on watch. Meal responsibilities were mapped out on a rigid schedule so everyone knew when to cook and when to clean, and we decided new watch schedules would be drawn out of a hat every week so that no one got stuck with a bad watch for too long.

The fact is, managing a crew of friends can be tricky because you want to please everyone and yet, as skipper and owner of the boat, your primary responsibility is to keep the boat and the crew safe.

Coming up with the boat rules can be a democratic process, but the final decisions should be based on what the skipper is comfortable allowing based on his/her experiences.

Those decisions may be disliked by paid crew but, ultimately, paid crew do what they’re told. When those decisions are disliked by friends on board, it can make things uncomfortable and more difficult to justify, as disagreements can have an emotional impact among friends.

There’s no easy solution to dealing with disputes on board a boat full of friends but, regardless, the skipper reserves the right to do whatever he/she feels is right. After all, it is his/her boat.

But I can say one thing I’ve learned in all this is, wherever possible, don’t try to take away a Frenchman’s Pastis.Save


Moroccan Henna: The Branding of a Gullible Tourist


After hours of walking through the winding maze of narrow streets that branch out from the center of the Marrakesh Bazaar, we finally reach a wide open space surrounded by tourist restaurants, snake charmers and roaming vendors who try desperately to push their trinkets into our hands in an effort to make an impromptu sale.

It’s here that I know I will inevitably end up paying too much money for something I don’t need.


Center of the Marrakesh Bazaar — view from above

Getting ripped off is something I always budget into the cost of visiting a new country, no matter where in the world it is. I like to think of the excess money I spend in those first few days in a new place as my “foreigner’s tax” – the price I pay for my ignorance until I learn my way around the exchange rate, the local economy and what the real costs are of certain basics like bread, beer and taxis.

I remember vividly every experience when I was conned traveling to a country for the first time – the taxi driver in Cairo, Egypt who agreed on a price of ten Egyptian pounds to drive me to the Pyramids then said, “Oh, I meant ten British pounds, not ten Egyptian pounds,” and then refused to let me out of the car until eventually I kicked my way out, threw 15 Egyptian pounds at him and ran off in such a hurry that he managed to hold on to my favorite music CD. There was the bartender in Montreal, Canada who reversed the exchange rate of the U.S. dollar to the Canadian dollar so that I paid twice the normal price for my drinks. There was the Russian babushka who sold me a bag of ordinary sticks and convinced me they were a special type of Russian tea. And there was the bus driver in Turkey who charged me ten times more than the local passenger rate, assuming I wouldn’t know the difference.


Marrakesh Market is full of eye candy

In Marrakesh, my foreigner’s tax comes in the form of an unwanted henna assault, which happens while I am trying to prevent a strange man from wrapping an enormous python around my neck.

As I try to peel the ten-foot-long reptile off my shoulders while nodding and smiling in an effort not to spook the snake, I notice my friends Kristi and Meg are having their hands stroked by two Moroccan women covered from head to toe in traditional garb. I use my friends as an excuse to escape the python and his handler but, before I can ask my friends what they’re doing, a woman grabs my arm tightly and starts drawing floral designs on my fingers with plastic tubes of brown henna.


Meg is both amused and unsure of what is happening

“Wait…no…what does this cost?” I ask Meg and Kristi, who have succumbed to the entrapment of the smiling, crooning Moroccan women sat squeezing brown paste on their hands as though they are decorating a cake.

Kristi looks particularly unimpressed as her covered assailant works quickly and forcefully, drawing brown, squiggly designs all up Kristi’s forearm. She laughs, “I don’t even know how this happened. I told her to stop…”

The henna-drawing assault is over in a few short minutes, by which point Ryan has wandered over to me to see what is being done to my arms. “What in the…did you want this?” he asks as I shake my head vigorously. “What is this going to cost?”

“Sheep! Very sheep price!” The henna lady responds. Five hundred Dirham only!”

I stand up from my stool and shout, “Five hundred Dirham? Are you crazy?! That’s fifty dollars!”

“Very sheep! Beautiful!” The woman smiles, holding my defaced arm up to Ryan, who looks like he might turn the woman upside down and shake her.

I grab Ryan by the arm and tell him I’m absolutely not going to pay five hundred Dirham. Yes, I was forced into getting a henna tattoo, but I would give the woman what I feel is a reasonable price. I pull out a one-hundred Dirham note and hand it to the woman, who immediately spits and swats my hand away. “No one hundred! Five hundred Dirham! This nothing for you!”

I walk away from the woman as she screams after me, and I slow down my pace, as I’ve been in this situation many times before. The feeling of being conned never absolves me from the feeling of guilt that comes with knowing that such desperate tactics are born of a need and a struggle to survive, to put food on the table and to make a meager living off the wealthy tourists that pass briefly through these countries, their pockets lined with cash to spend on good food and souvenirs to bring home.

I turn around and face the woman shouting at me. “I will give you one hundred Dirham or I will give you nothing. Your choice.” I wave my arm at her and say, “This was not my choice. One hundred Dirham is generous.”

“No good!” The woman screams. But she grabs my one-hundred Dirham note and spins on her heels, walking away to grab another unsuspecting tourist in the market square.

Meg and Kristi walk up next to us with their heads hanging low. “How much did you give them?”

“Two-hundred fifty Dirham.”

“Twenty-five DOLLARS?!” Ryan explodes.

Kristi and Meg shrug their shoulders sheepishly as they say, almost in unison, “I felt bad!”


Our gullible tourist stamps on full display

I laugh, sympathizing with how the henna transaction has made us feel; like we’ve been violated and branded with the tattoo of a gullible tourist, which we would wear with shame for the rest of our time in Morocco.

But, mentally, I reconcile our over-payment as a donation to local families in need. And I write off my foreigner’s tax as a necessary lesson in navigating the markets of Marrakesh: never let a man wrap a snake around your neck and never let a woman tattoo your arm without your permission.


I prefer the beautiful things I choose to buy over the ones I’m forced to pay for



Morocco Markets: Objects of My Desire


Sailing into Rabat, Morocco

It was hard to focus on helming as we pulled into the harbor in Rabat, Morocco, as I stared with wonder at the ancient stone structures lining the right side of the entrance and the colorful wooden fishing boats bobbing up and down on their moorings. I sensed that we hadn’t just left Europe; we’d sailed into another era from the distant past.

Fishermen working on their little boats stopped for a moment to stare at Cheeky Monkey as we motored past. A few men smiled and waved and I wondered whether they were transfixed by the arrival of a foreign vessel or the spectacle of what appeared to be a female-run boat with me at the helm and Kristi and Meg preparing the fenders and lines for docking at Bouregreg Marina. Ryan, the male minority on board, was on the radio getting docking instructions from the marina while I looked around and noticed the lack of women on the many boats we passed in the harbor. I smiled and waved at the fishermen as their mouths hung open, their jaws involuntarily unhinged.


Our jaws also hung slack as we pulled into this cute harbor in Rabat.

We weren’t sure what to expect from a marina that only charged $15/day for a 44-foot catamaran, but we definitely weren’t expecting a welcoming committee of eight officials to step on board bearing gifts of baseball caps, pens and key chains emblazoned with the marina’s logo for each of the crew. Two of the officials excitedly thumbed through our passports and asked us questions about ourselves and how on earth we could all survive without jobs, while the other officials on board looked around silently. I wondered if the extra men were having a dull day in the office and so they decided to tag along just to have a closer look at the boat and its crew.

Our amusing clearing-in experience motivated us to get off the boat and go explore what Morocco had to offer beyond the waterfront of Rabat. So once our French friends, Morgan and Xavier, arrived from Paris, ready and packed for the Atlantic-crossing, we shut up the boat, rented a car and hit the road on a mission to go see Casablanca and Marrakesh, two cities that were near enough to explore in the three days we had spare before sailing away to the Canary Islands.


Xavier and Morgan were thrilled to join us in Rabat for our Atlantic crossing.

Morocco markets: Shopping in Casablanca

I’m sure Casablanca has a lot more to offer the keen tourist than just bazaar shopping, but as we only had a few hours to stop there on our way to Marrakesh, we dove into the heart of the traditional marketplace in an attempt to absorb our surroundings in the most efficient way possible. We were aiming to shock our senses and dive into the experience of our sudden departure from Europe.


The best way to dive into any foreign culture is to EAT!

The crafts displayed in tiny market cubicles formed a tapestry of colors, textures and smells that drew me in as soon as we walked through the gates of the Casablanca Bazaar. There was silver jewelry with colored stones, carts piled high with roasted almonds and dates, handmade leather bags and slippers dangled above our heads, all of them too beautiful not to reach out and touch. Vendors pleaded for us to come have a closer look at their wares in their direct but gentle way, looking us in the eyes and smiling as they held out pretty objects to entice us into their shops as we walked past.


“Must touch…so pretty…how much are they?”

Before we even got a few steps into the market, Meg and I were drawn to a stall that was intricately stacked with polished wooden boxes of all shapes and sizes. The boxes begged to be touched and opened and held, and the vendor took full advantage of the power of his beautiful handicrafts by encouraging us to try and open one of his many “magic boxes,” clever little cases with hidden keys that required puzzle-solving skills to find. Without knowing what we would need a magic box for, and before Ryan could complain that little wooden boxes have no use on a boat, Meg and I bought three of them.

Resisting the irresistible

It’s moments like these when I long to be able to collect things, when it seems like a shame that I can’t keep much on a boat. I ran my fingers through the multi-colored woven cloths and reached up to touch the gleaming brass lamps above my head and, for a second, I wished I had a house I could fill with unique objects from Morocco. But then I remembered that being free to roam means being able to carry everything I need in one bag or on one boat. I remembered that shedding objects and leaving the weight of possessions behind is what has allowed us to keep moving from one beautiful experience to another.


So many beautiful things and so little room to keep it all.

And with that thought, the shiny brass lamps, though beautiful, transformed into heavy burdens that would require somewhere to be housed and someone to polish them. So I pulled my hand away, smiled at the vendor and kept walking.


This is Meg. She has a large family and 3 sisters, so she bought everything.


Update from Tasha

Hey everyone!

Thanks so much for reading and having patience with the lack of postings while I’ve been moving around in areas with poor WiFi. Life on a boat means we’re often not connected, which has its pros and cons. But from the perspective of a blogger and YouTuber, they’re mostly cons. I have learned to switch off and be patient every now and then, but it’s a struggle – I’m constantly chasing down SIM cards and data in remote islands.

In any case, if you didn’t catch our video about Morocco on Chase the Story Sailing, catch it here:

Thanks so much for reading and watching – don’t forget to hit the red subscribe button on YouTube so you don’t miss an update!





Cheeky Monkey is Seeking Adventurous Crew!


Announcement: Cheeky Monkey is sailing across the Pacific Ocean!


We are looking for crew!

S/V Cheeky Monkey is about to embark on the ultimate sailing adventure from the Caribbean to Panama to the Galapagos to the South Pacific islands and we are seeking the right crew to join us on this adventure!

If you’re a Turf to Surf Newsletter subscriber, you may remember me recently writing that “I’d like to slow down in 2016 and look around more” – well, that outlook lasted a whole month before we decided we’d had enough pause and, instead of spending a year in the Caribbean on Cheeky Monkey, we’re heading towards the South Pacific instead! (By the way, if you haven’t yet subscribed to my monthly newsletter, you can do so here at Turf to Surf’s Subscription Page by entering your email address.)

If you’re interested in crewing for us and want to find out more about us (Tasha & Ryan), the crew we’ve had on board so far, and the kinds of adventures we’re out chasing, catch up on our story by watching our YouTube Channel, Chase the Story: www.youtube.com/chasethestoryaroundtheworld


So, let’s get down to it — are you the next crew member we’re looking for to join the party on Cheeky Monkey?

Have a look at the list of qualities we’re looking for below, and let us know if you’re serious about joining us on this adventure!

Essential Qualities

  • Adventurous
  • Good sense of humor
  • Open-minded
  • Young at heart
  • Fun
  • Sporty
  • Friendly
  • Easy-going
  • Good personal hygiene
  • Not allergic to or afraid of cats


Extra Qualities

  • YouTube creator / Videography experience
  • Creative abilities
  • Social Media / PR expertise
  • Sailing experience
  • Good at fixing things
  • Good chef
  • Good at water sports (and are willing to teach us some things)

Application Requirements

  • Please submit the following 2 items by email: (1) Answer the question “Why do you want to be a part of this adventure?” in the form of either a 2-minute personal video (include link to video) or a 300-word personal written statement. And feel free to be creative with your answer and how you choose to answer it either in video or in words. (2) Resume / C.V. – we ask for this because we want to get an idea of your professional experience and/or adventuring experience.
  • Application Deadline: March 23rd, 2016
  • Email submissions to ryan@turftosurf.com


  • How much will it cost? You only need to cover the cost of your flights and any personal necessities you care to purchase in ports. Board, food, booze and adventures covered by us.
  • How long will I be crewing for? No adventure of this magnitude can be achieved on a two-week vacation. We are looking for crew who can commit to a crossing or two.

Crew Expectations

  • All crew share equally in the duties on board Cheeky Monkey, including keeping watch, cleaning, cooking, maintaining the boat, repairs, provisioning runs and cocktail making.
  • We expect crew to contribute to the creative process on board, using whatever skills they have or are willing to learn – i.e. video-making, posting on social media, photography, website building, etc.
  • We expect crew to have fun and enjoy the adventure!

Note from Tasha & Ryan

We look forward to hearing from you and getting to know more of your story! We’ve had great experiences so far with crew on board who embody all the qualities we’ve listed above. So let us know if you’re the missing link in this next great adventure — we’d love to meet you! Or if you know someone who would love to sail with us on Cheeky Monkey, share this opportunity with them!


Tasha & Ryan




Sailing to Morocco: Stress in the TSS


As we quickly tidied up the boat to get ready to sail from Gibraltar to Rabat, Morocco, I examined the charts closely to understand the route we would be taking across the busy traffic channels in the Strait of Gibraltar. There were so many frighteningly large ships moving across the screen on AIS that our chart plotter looked like an arcade game of Frogger with red-outlined vehicles moving in two organized streams, threatening to squash me as I tried to move across the strait.


If you were a child of the ’80s and ’90s, you might remember the game Frogger.

We would have to pull in with the traffic flow going west, then nudge ourselves slowly south until an opening appeared wide enough for us to make a 90-degree bee-line across the hectic traffic separation scheme (TSS) to the north side of Africa. But I’d been watching the cargo ships moving quickly across the screen for the last half hour and there didn’t seem to be many opportunities for our small cruising ship to cut safely from one side to the other.

There are few places in the world where you can find commercial traffic as heavy as it is in the Strait of Gibraltar, a narrow conveyor belt running ships between Europe and Africa. But New York Harbor, where I first learned to sail, is one of those busy ports, so I wasn’t overly concerned about the traffic we’d be encountering. After years of sailing in and around New York City, we were used to being constantly vigilant, tacking and weaving between cargo ships and ferries as we made our way out to Sandy Hook to anchor for the weekend or headed up the Hudson River for the day.


Ryan, keeping a lookout for oncoming traffic to avoid.

When we first started sailing, we conversed with every experienced sailor we met, collecting tips on weather, navigation, engine trouble and sailing to faraway places. And we were surprised at the number of times we were told “never sail at night if you can help it; it’s very dangerous.” We laughed because night sailing in New York Harbor was one of our favorite pastimes. With the famous Manhattan skyline lit up along the Hudson River, our boat was always blanketed in the glow of the city as though we were sailing under a hundred moons. What was everyone talking about – “sailing at night is dangerous”? Sailing in the busy traffic of New York was all we knew at that time, so it hardly seemed dangerous to us.

It wasn’t until we sailed out of New York to the Bahamas and the Caribbean in 2012 that we realized how little boating traffic exists out there when you move away from New York Harbor. If you jump out on the ocean, you see less than a handful of boats a day. If you stay inside the Intracoastal Waterway, you might spot a few more boats, but between ports, traffic is scarce compared to the areas around New York City.

As I nudged the bow of Cheeky Monkey out into the Strait of Gibraltar, however, I was reminded how heavily surrounded with traffic I once was and how blissfully spacious the seas have been since we left New York. Pulling into oncoming cargo ship traffic in the strait was suddenly foreign and stressful and required being vigilant to the movements of hundreds of ships who all had right-of-way over our slow-moving vessel.


These ships may look heavy and slow-moving, but they bear down quickly.

Kristi and I sat at the helm, examining the AIS information of oncoming vessels and ships who approached quickly from all directions, trying our best to navigate a path that would be the least nuisance to the priority commercial traffic surrounding us.

As we traveled west along the south coast of Spain with the flow, it seemed like there was never going to be a break in the shipping lanes to get us cleanly from one side of the purple TSS band, which was marked clearly on the chart plotter, to the other. So we took the first small opening we had to turn Cheeky Monkey at a 90-degree angle to the TSS.

To me, the TSS on my chart plotter looked narrow and easy enough to cross, though the traffic on either side of the purple band seemed to still be speeding densely at us in both directions. TSS traffic flows like a highway – the north line of traffic moves from east to west and the south line of traffic moves from west to east. My challenge was to get across the traffic moving west to east at speeds three times faster than Cheeky Monkey so that I could continue moving southwest along the coast of Africa without getting in the way of anyone.

So once Cheeky Monkey’s little ship icon reached the other side of the purple band on my on-screen game of cargo-ship Frogger, I breathed a sigh of relief and turned the boat to head southwest again. Which is when a loud, stern voice came over VHF channel 16 saying, “Cheeky Monkey, Cheeky Monkey, Cheeky Monkey, you are to maintain a 90-degree angle until you cross the TSS!”


Bird’s eye view of the Strait of Gibraltar from a scenic point in Gibraltar.

I looked at Kristi, confused. “We crossed it, didn’t we?” We zoomed in on the chart and looked again at the purple band marking the traffic zone. I was pointing to a purple line running across the screen when Kristi zoomed out and pointed to a second purple line running across the bottom of the screen just north of the coast of Africa.

“Whoa! I thought that purple band there was the TSS! It goes from that band to the other band?” I said, with my hand moving up and down the length of the screen. “Shit!”

I had suddenly realized my mistake when the radio piped up again, “Cheeky Monkey, Cheeky Monkey, Cheeky Monkey, what are your intentions?”

“Um, we want to go to Morocco?” I responded into the radio, flustered, as Kristi laughed hysterically at the ridiculousness of my answer. Put on the spot, I had no idea what the yelling man meant by my “intentions,” but it probably wasn’t a diary of my day’s plans, or what I was craving for lunch.

Having realized I had not, in fact, crossed the traffic separation scheme, I turned Cheeky Monkey back to a 90-degree angle and continued on a hair-raising path cutting between cargo ships, putting both engines on full throttle and speeding towards the North African coast as fast as I could go to avoid being hailed on the radio again.


Cheeky Monkey, pulling into the harbor in Rabat, well away from the TSS traffic.

99% of the time we are out sailing, regardless of the waters we are in, there is ample room to maneuver, deal with mishaps, change course and relax, allowing the direction of the wind to dictate the course towards our next destination. It’s often a peaceful, slow-moving process with our boat sailing along comfortably at a humble 6-7 knots with no one else on the horizon.

But the traffic separation scheme in the Strait of Gibraltar jarred me out of that peaceful reverie and reminded me that vigilance and precision are paramount where traffic is dense and strict rules govern a safe crossing. We’d been sailing in empty waters for so long that I didn’t properly anticipate how heavy the traffic would be getting from Spain to Morocco.

If sailing in the New York Harbor was like getting to Level 3 of Frogger, then the Strait of Gibraltar was Level 10. And I didn’t have enough practice in this game to remember how not to get smashed by an oncoming vehicle. Luckily, we got safely across the TSS and pulled into Rabat with no harm done. But next time I might just review my book of navigational rules before diving into the shipping lanes again.


Once we got south of the TSS, it was smooth sailing all the way to Rabat, Morocco.