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.

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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…

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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 should add to this post that if you’re thinking of buying a Fountaine-Pajot catamaran, you should reach out to me at tasha (at) turftosurf.com — 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.

Though, I have to admit I’ve gotten a little side-tracked lately by telling stories on video.

So, if you haven’t seen all 22 of our video stories so far, join the 18,000+ subscribers on our YouTube Channel, Chase the Story, for weekly video updates. I’m having a lot of fun reliving this journey we’re on through the films we make.

And if you don’t already follow the story of Cheeky Monkey sailing around the world on my other media, here’s where you can find me:

Instagram: @turftosurf

Turf to Surf Facebook

Twitter: @turftosurf

Chase the Story Facebook

Thanks again, everyone, for reading, watching, following and supporting this little dream of ours.



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 arrived 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

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.

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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…

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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.

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.

Cheeky Monkeys in Gibraltar

It’s always a little nerve-wracking pulling our 24-foot-wide catamaran through a narrow entrance, past the sharp bowsprits lining the docks with what feels like just inches to spare. But, luckily, as big as our boat is, with two engines, Cheeky Monkey turns on a dime, so I had little trouble nudging our boat safely up to the scary concrete wall in the Queensbay Quay Marina in Gibraltar Harbour. I was sweating a little as I did it, picturing our nice fiberglass hull crunching up against the high stone if I maneuvered badly. But with six crew in total, we had plenty of people at the ready with fenders in hand, and I was able to pull our boat gently up to the harbor wall without incident.

With a population of just 30,000 people, Gibraltar feels like a small English village that’s been airlifted out of Britain and dropped on a spit of land in the south of Spain. Lining the Gibraltar Harbour, there is a string of waterfront English pubs with red-faced patrons drinking pints of beer from sweating glasses and iconic red phone boxes on every street corner, though the mix of Spanish, British English and Arabic being spoken in the shops gives this quaint English village a much more multicultural feel.

We weren’t planning to stay in Gibraltar long, as we had a deadline to get to Rabat, Morocco in a few days to pick up our friends Morgan and Xavier, who were flying in from Paris to do the Atlantic crossing with us. But we also didn’t want to leave Gibraltar without going to the top of the Rock of Gibraltar and seeing the Barbary Macaques, the famous wild monkeys that live on the rock.

I mean, you can’t pull a boat called Cheeky Monkey into a port that’s famous for monkeys and not go see some monkeys, am I right?

So the morning of our departure from Gibraltar, crewmates Kristi, Meg and I went on a mission to get to the top of the Rock so we could squeeze in a whirlwind tour of Gibraltar before jumping back on the boat and rushing off to Morocco.

Originally, we had grand ideas of running to the top of the rock for some exercise plus sight-seeing (you know, kill two birds), but we came to our senses, scrapped the exercise idea and dashed off to catch the last cable car, only to find it wasn’t running because of the high winds. So instead we found ourselves in a tour bus with a group of Spanish-speaking tourists, being driven up a hill so ridiculously steep that I think all of us were glad we didn’t decide to run up it. I like a challenge, but that challenge would have taken us a lot longer than the two hours the bus took, and I’m not sure we would have had much energy to get the boat ready after that.

When our bus reached the top of the hill near the Rock of Gibraltar, I wasn’t expecting to be immediately surrounded by monkeys, or that the monkeys would be so fearless as to jump on the cars and, at one point, Meg’s head. These were intrepid, rather cheeky monkeys (*wink*), which delighted me to no end, but raised some anxiety in Kristi, who showed us a scar on her arm where she was once bit by a monkey.

Even without the monkeys, the views from the top of the Rock were worth the trip alone, so if you ever find yourself pulling into Gibraltar for just a day, make sure to get yourself to the top of the hill — this is what you’ll see:

gibraltar view cheeky monkey sailing around the world sailing blog

The bus stopped halfway up the hill so we could get this view of Africa.
sailing blog cheeky monkey gibraltar turf to surfMeg, Kristi and me at the halfway point. We’re smiling because we didn’t run it ?
gibraltar cheeky monkey sailing around the world turf to surf
I wonder if the rental car companies in Gibraltar charge for monkey scratches.

monkeys gibraltar sailing around the world turf to surf

Baby monkey! Who doesn’t love baby monkeys? (Kristi, maybe).

cheeky monkey gibraltar turf to surf sailing around the world

 Meg might not be a big fan of monkeys after this trip, either.
rock of gibraltar mediterranean sailing around the world cheeky monkeyThe Rock of Gibraltar, which we’ve seen from sea and now we’ve seen it from land.
monkey on rock of gibraltar sailing blog turf to surfThis monkey has a pretty spectacular backyard view.
spain gibraltar sailing around the world turf to surf sailing blogThis sign appears to be saying “Spain is that way, so walk this way instead.”


Update from Tasha

Hey everyone! If you didn’t catch the video Kristi made about our tour of Gibraltar, check it out here!

We post a new video weekly, so subscribe to our YouTube Channel, Chase the Story, so you don’t miss a single update!



The Gift of guests: sailing for the first time (again)

the gift of guests sailing for the first time sailing blog

I am sitting in the cockpit of Cheeky Monkey, enjoying an evening glass of wine with a view of several thousand gleaming boats in the Real Club Nautico Marina in Palma de Mallorca, when I get a message from my friend John saying, “I’m ready!” just as this picture comes through my phone:

sailing for the first time cheeky monkey turf to surf

I start laughing and immediately reply that Ryan and I are awaiting John and his partner Chris’ arrival to Palma with excitement – after all, it has been over 10 years since we lived just around the corner from them in Sevilla, Spain, where we taught English for a living.

I sip my wine, smiling, because this is the reason we chose such a large boat for ourselves – it wasn’t so much for us alone, but for the opportunity to bring friends on board for any leg of our journey around the world. And now it seems the dream we had of sharing our journey with loved ones is becoming a reality.


By the time we finally sold our businesses (teacher training schools and English as a Second Language schools in the U.S.) in February 2015, Ryan and I had been making our rounds to boat shows, shopping for what we dreamed would be the boat that would take us around the world one day.

Our first boat, Hideaway, had given us some of our best years in New York, teaching us to sail and to fix engines, tearing us away from the stress of building and running our own companies and inviting us to dream of what the future could hold if we ever decided to close the entrepreneurial chapter of our lives and do something completely different.

sailing for the first time again hideaway turf to surf

Our old Catalina 34, Hideaway, in the Bahamas.

And when that opportunity arose in the form of a signed Sales Purchase Agreement for both of our companies, we scrapped the boats on our what-we-can-afford-if-the-companies-don’t-sell list and we immediately plunged feet-first into the dream of sailing around the world on a Fountaine-Pajot Helia, a boat with more than enough room to have friends and crew comfortably on board as we sailed to countries that sparked our wanderlust and brought us back to the basic dreams that kick-started my and Ryan’s careers in teaching ESL: to travel and learn about the world through our travels.


When John and Chris hop out of their airport taxi in Palma, I’m surprised to see they’re not wearing their wetsuits and snorkels already. But soon after they arrive to the docks, they are jumping up and down like excited children, gasping at the boats surrounding them, as well as every detail of our new floating home.

No matter what lifestyle we choose, whether it’s living in an apartment in a big city, a house in the rice paddies of Bali, a log cabin in the woods or a boat that’s forever on the move, there’s always an initial thrill over the change in environment. But then that thrill eventually gives way to a daily routine that’s filled with menial tasks and friends who live the same lifestyle as us. Which means, at some point, the life we’re living slowly begins to feel completely normal. This is a good thing, of course, as it would be exhausting to wake up every morning with a distracting feeling of euphoria, causing me to fawn and delight over every detail of my mind-boggling and extraordinary day.

I mean, I’d never get anything done otherwise. “Honey, do you want breakfast…OH MY GOD! Have you seen this TREE?! It’s growing avocados! I’ve never seen an avocado on a tree before! Wait, what was I doing?”

It’s like falling in love – if we forever remained in that ecstatic love-sick state that we experience at the beginning of a relationship when we can think of nothing else but being near our lover, then we’d never be able to hold down a job.

Ecstasy gives way to a much more comfortable feeling of normal fondness, so we can all go about our day getting things done again. And that normal fondness is the feeling we have settled into regarding our new boat and our newfound freedom.

But then John and Chris arrive on a plane from Sevilla, wearing nautical-themed clothing and grinning from ear to ear.

“OH MY!” Exclaims Chris as we give her a tour of the galley. “Look, John! They even have storage in the floor! How amazing!”

John and Chris flit from one corner of the boat to another, amazed at the economy of size of everything on a boat, as well as the views from the deck, the steering wheel at the helm and the electronic instruments everywhere. They are excited by every little detail and their enthusiasm is wildly infectious. It has the effect of reminding us that, though our lifestyle has become normal to us, living on a boat is an extraordinary thing to experience for the first time.

the gift of guests sailing for the first time again sailing blog

Chris and I, making dinner in the galley of Cheeky Monkey.

Watching John and Chris on their first sailboat is like watching someone fall in love for the first time – I see the sparkle in their eyes and though I know the feeling will calm down eventually, I don’t want to spoil it for them. The joy they’re experiencing in the moment expands in the space around them and blocks the thoughts running through my head of the head that’s leaking and the sump pump that doesn’t work.

Within a day of John and Chris arriving to Palma, two more guests arrive who will be staying on board Cheeky Monkey through our Atlantic crossing. We met our friends Meg and Kristi when we were participating in the ’13-’14 Clipper Round the World Yacht Race, which Ryan and I did a few legs of while Meg and Kristi did the full round-the-world circumnavigation.

But even for experienced sailors like Meg and Kristi, who have lived on stripped-down 70-foot racing yachts for nearly a year, stepping on board a cruising boat like Cheeky Monkey is a new experience. For one, you won’t find an espresso machine, hot showers or an ice-maker on board a racing yacht.

Mind you, you won’t find an ice-maker on board our yacht either, but that isn’t because it’s not supposed to be there. It’s just that ours still doesn’t work. I know, I know, #firstworldproblems

The joys of simple land-pleasures like comfortable seating, a queen-sized bed and a large dinner table are the things that excite Meg and Kristi when they step on board Cheeky Monkey for the first time, which makes me remember how bare and uncomfortable my boat Henri Lloyd was on the Clipper Race. Over the next few weeks, we will find ourselves saying, “This ain’t the Clipper Race!” often and with great delight.

With 6 crew on board, Cheeky Monkey, we pull out of Palma bound for Gibraltar, setting up a watch system where each of us is responsible for two hours on deck in daylight and two hours in the night, allowing for plenty of sleep and relaxation time for the crew.

Except John and Chris, who are only on board for three days, forgo most of their sleep to stay up and watch for possible marine life on the horizon.

gift of guests sailing for the first time again sailing blog

This is pretty much where Chris and John stood for 3 days straight.

One night, I groggily step into the galley in the pitch black of night to get a drink, when I hear John scream “Tasha! Come here! I think I see dolphins!”

I have only ever seen dolphins at sunrise and sunset and have never seen any sign of them in the dark, so I assume John is just seeing some flying fish jump out of the water.

John has a spotlight in his hand and is shining it on the water where, sure enough, a fin pops up above the smooth, black surface of the water.

“Oh wow!” we all squeal in unison.

“How long have you been out here looking?” I ask, rubbing my eyes.

“All night!” screams John as Chris bounces up and down next to him. “We’re too excited to sleep!”

Just then another dolphin pops up into the wake under the foredeck trampoline and all three of us rush to the bow to stare at the water beneath us.

“Look! There’s more!” screams John. “Should we wake Kristi?”

I look at my watch, which says 3 am, and laugh. “I think Kristi’s seen plenty of dolphins on the ocean before.”

“BUT HAS SHE SEEN THEM AT NIGHT?!” John shouts, running back to the cockpit. “I’m going to wake her!”

Shortly after, Kristi stumbles out to the foredeck, rubbing her eyes, as John and Chris are bouncing up and down on the trampoline screaming, “Look! There’s another one!”

To which Kristi laughs and says, “I’m going back to bed,” leaving me alone on deck with John and Chris, shrieking and pointing, filling the night air with the joyful noises of hysterical adults.

dolphins sailing again for the first time sailing blog

Chris, capturing a rare sight of pilot whales on the Mediterranean.

Normally, I like to spend my quiet night watches immersed in my introspective routine of reading and writing while the rest of the boat sleeps. But tonight is not a routine kind of night. It’s a night filled with the first experiences of jubilant friends who, for a few days, I get to share my extraordinary life with.

So, rather than retreat to my routine, I toss my book aside and I lay on the trampoline with John and Chris as we watch dolphins dive and swim beneath us, covered in a sheath of glowing green glitter as their bodies cut through the phosphorescent water, leaving a spray of fireworks in the air every time they jump out of the water.

Our faces are softly lit by the moon as we stare patiently at the water, waiting for the next astonishing thing to take us by surprise.

It’s true, I wouldn’t get much done on any of my night watches if I spent them all lying face down, staring at the water with big eyes full of wonder. But, in this moment, I’m grateful for the gift our guests have brought us – the gift of experiencing something extraordinary for the first time, again.

guests sailing for the first time again turf to surf
John, holding up his first catch. He smiled like this for 3 days nonstop.


Update from Tasha

Hey everyone! If you haven’t yet seen our video of John swimming with pilot whales on Chase the Story, our YouTube Channel, check it out here! I promise it will make you smile:

And if you like it, click the SUBSCRIBE button so you don’t miss our weekly updates! We’ve been working hard on editing videos so we’d love it if you could share it and give us feedback in the comments!

Thanks everyone for reading and watching – I really appreciate it!



7 lessons learned catching our first fish

7 lessons learned caching our first fish thumbnail

“Fish on!” I hear John scream, slowly nudging me out of a deep sleep below deck.

I pull on some clothes and rush up on deck to find Ryan running around the cockpit, desperately searching for something. “We don’t have a gaff! Wait, I have a trident!” He pulls a long-handled deck brush out of the lazarette. “No, that’s not it!”

The look on Ryan’s face is that of pure delight — it’s our first fish while trolling and he’s determined not to let this one go. Meanwhile John is standing at the stern, pulling in the line on the hand reel while Ryan flits anxiously around the cockpit, finally locating a net to scoop up the fish with. With a couple of swift tries, Ryan and John pull the flopping tuna into the cockpit and start jumping up and down, whooping with disbelief and excitement.

“Who’s going to kill it?” asks John.

john harrop fishing cheeky monkey 7 lessons learned turf to surf

Our friend John, clearly dressed for a fishing adventure.

When our friends John and Chris turned up in Palma de Mallorca to go sailing with us to Gibraltar, they couldn’t believe that in the 15,000 miles we’d sailed that we’d never caught a fish on our boat before. I wouldn’t have believed it either, but I knew what terrible fishermen we were and, truth be told, we hadn’t really tried much. And the few efforts we made only resulted in a tangled ball of seaweed at the end of our line.

For some reason, killing and filleting fish is my job, so once the tuna lands in the cockpit, I get down to the business of putting this fish out of its misery and preparing the kitchen for a sushi dinner.

What I don’t know, however, as we’re fumbling around trying to kill and fillet our first tuna (and a second, even larger tuna a few hours later), are all the mistakes we’re making as we try to land and kill a fish while under sail.

So thanks to all the advice from the expert fishermen commenting on our YouTube Channel, Chase the Story (see the video of our fishing exploits here: https://youtu.be/RyqiL755L-A), these are all the things we did wrong. We’re always learning something new from the sailing community, so if you have anything to add to this, feel free to comment. We might even share some of our sushi with you if your tips turn out to be helpful.

In the meantime, here are 7 rudimentary lessons we learned while catching our first fish on board Cheeky Monkey:

1. Slow the boat down

As newbies to fishing, we got so excited about landing our fish that it never occurred to us we were going too fast to make that happen. I mean, who has time to drop the sails when…FISH!

Also, I didn’t realize how big the fish would be in the Mediterranean and a number of the big ones we snagged got away because there was too much drag on the line, pulling the fish clean off the hook.

What we’ve learned we should do when we hear someone scream “Fish on!” is down the revs if we’re motoring, or luff up, if we’re sailing. That will lessen the drag on the fishing line and make it easier to reel in and land the fish.

2. The net goes in front of the fish, not behind

It seemed like an intuitive action to scoop the fish up from behind, but we had a few comments that advised us to put the net in front of the fish, as the fish will always swim forward and away from the net if you put it behind the fish. Plus, you’re not fighting the drag through the water if the net goes in front.

It makes sense now, but that never occurred to us. And with the second tuna we caught, we found it impossible to net the fish, it was so fighting so hard. Which leads to our next mistake…

tunafish 7 lessons learning catching our first fish

Our first little guy was easy enough to net. But the big guy after him? Not so much.
3. Have a proper gaff on board

We didn’t have a gaff on board at the time we caught our first fish (we do now). What we had was a trident, or as Ryan calls it, “the Neptune thingy.”

The trident kind of worked on our big tuna (estimated 16 kilos) when it was alongside the boat and we were struggling to land it. I managed to get close enough to stab it with the trident, which caused the fish to bleed out a little and took the fight out of him long enough for us to drag him on board by hand.

4. Alcohol is for drinking, not for killing fish

I’m sure I read somewhere that you should always have a cheap bottle of vodka handy for killing fish, so that was the first thing I thought of when our fresh catch was flopping around the cockpit, trying to work its way back to freedom.

I poured some vodka in its gills, but it didn’t seem to do much. Some commenters have pointed out that this is a cruel way to kill a fish, and we should just cut its head off quickly and put it out of his misery. That’s what we did in the end, but there was a torturous period when we were trying to inebriate the poor fish to death. Rather than kill the tuna, the vodka seemed to turn him into an angry drunk.

5. Tuna bleeds like a stuck pig

Our cockpit looked like a CSI crime scene by the time I was done with our tuna. Some people have suggested that we cut off the head and then drag the tuna behind the boat until it bleeds out. It’s less messy and apparently it makes the fish taste better?

I have no idea, but I’ll try that next time. I’m hoping, at the very least, it will save me a few hours of deck scrubbing.

tuna catch 7 lessons learned catching our first fish

This is by far the biggest fish we’ve ever seen. Now, what to do with it?!
6. The best way to fillet a fish varies widely by type of fish

So far, we’ve only ever caught tuna and Mahi Mahi on our boat and the cleaning process is quite different for each, as I’m sure it is for every fish.

Tuna has an interesting bone structure, so I discovered the best way to fillet a tuna, once you’ve sliced its belly and pulled out all the guts, is to run the knife along the bone, which is an L-shape kind of structure. You get the most meat out of the fish that way, and it comes out in nice, fresh substantial steaks.

With Mahi Mahi, the skin is really tough and I’ve found it doesn’t cook as nicely with the tough skin left on it. But skinning a Mahi Mahi is a time-consuming process that requires a few tools that I wouldn’t normally keep in my fishing box.

I have no idea if this is the best way to skin a Mahi Mahi, but what I found easiest was to start the skinning process by running my filleting knife under the skin about an inch from where we cut off the head. Then once there is a lip of skin lifted, I use a pair of long-nosed pliers to cinch the edge of the skin. I then roll the pliers towards the tail, twisting the skin around the pliers kind of like I’m opening an old-fashioned tin of sardines. This allows me to roll most of the skin straight off the surface of the Mahi Mahi. I use my filleting knife, as well, to help slice the skin away from the meat as I roll the pliers.

fillet tuna 7 lesson learned catching our first fish

I may look like I know what I’m doing, but really I don’t.
7. The disco squid lure is a winner every time

We’ve tried dozens of different trolling lures to catch fish over the years without much success. But then someone advised we get a “disco squid.” Every single fish we’ve caught on board Cheeky Monkey has been with one of these guys. Maybe there are other lures out there that work, but I have no idea what they are. Day-glo Dave, as Ryan calls this guy, is our lucky lure from here on forth.

7 lessons learned catching our first fish turf to surf

We affectionately call this little guy “Day-glo Dave.”

We are painfully aware what novice fishermen we are, but we are fish lovers and sushi connoisseurs. And being half-Korean, I feel a responsibility towards my heritage to perfect my sushi techniques from the sea to the dinner table.

Which brings me to my recommendation of this incredibly efficient and easy-to-use sushi-rolling device. I found this in a fancy home store in France, after multiple failed attempts trying to roll sushi using a bamboo mat. This thing is amazing and has changed my sushi-making life for the better. It means I don’t spend hours in the kitchen swearing and throwing rice at the walls. Seriously, everyone needs one of these (Amazon.com link below):

sushi 7 lessons learned catching our first fish

It took the crew less than an hour to throw together this incredible meal.

We still have a lot to learn about catching, preparing and cooking fish on board Cheeky Monkey, but I think we’re off to a good start.

Let us know how we’re doing and if you have any helpful suggestions. That is, unless you’re this guy:

fishing youtube comment

In which case, go home, Almon Gulley Stomppers Roberts, you’re drunk, YALL is not a word and your keyboard is stuck on all caps.