Inside A Traveler’s Walls: Tasha & Ryan


It is time for another amazing traveling family, to be more specific, a sailing family. The Turf to Surf family consists of Tasha, Ryan and a couple of adorable cats. Cats on a boat, yes!

Just being on a boat stimulates my imagination ~ Tasha

Can they get coolest couple ever award right now? I will let you in on a little secret before you begin, these two once had careers in NYC, pets and a big city lifestyle to support, but they found a way. They have traveled on $3,000 for 9 months, ventured to what most people would consider dangerous countries and found ways to bring their two cats on many of the journeys. It’s possible and these two innovative adventure seekers are living proof.

Wait until you hear the back story which led them to the life they have now. It started with years of travel that prepared them for a business opportunity which prepared them for their next adventure. As you read this you will see that they put a lot of hard work into obtaining this less than traditional lifestyle because they believe in it and they want the adventure to continue.

Of course I cannot help but mention that they are planning on raising children on the boat. You all know I love the idea of children and travel. I think these two will do a fabulous job raising adventurous, and inquisitive boat babies.

Lets give Tasha and Ryan a virtual high-five for going after those dreams and taking the road less traveled.

Ok, enough of my chatting, grab your coffee and get comfortable. It’s time to be inspired by this sailing family.

Sailing Family

sailing family

3. Tasha with backpack in 2014 in Indonesia

4. Cheeky Monkey at anchor

4. Cheeky Monkey in Palma de Mallorca

5. Outdoor Cockpit Cheeky Monkey

5. Outdoor Cockpit with Friends

Introduce us to the people you live with? 
I live with my British husband Ryan and, often, friends or crew we’ve picked up along the way for parts of our journey around the world. I met Ryan 11 years ago in Doha, Qatar, where we were both teaching English at the time. Both of us had spent many years traveling, back-packing and supporting ourselves by working abroad. I primarily worked teaching English as a second language and Ryan had tried his hand at a number of different things like bartending, construction work, journalism, selling yachts and teaching English…whatever he could do to fund his travels, he did.

Sailing was entirely Ryan’s idea. I grew up in a land-locked town in upstate New York and had only ever been out in rowboats on lakes. I didn’t even know people lived at sea on sailboats until Ryan mentioned one day, early in our dating life, that it was his dream to sail around the world. Which sounded absolutely crazy and — considering how little money we had at the time — completely unattainable, in my mind.

Where are you in the world and what are you living in?
Right now I am in Morocco. Just yesterday we sailed our boat to Rabat from Gibraltar with two crew on board, our friends Kristi and Meg, who we know from doing the Clipper Round the World Yacht Race a few years ago. We’ve also just picked up two more friends, two French guys named Morgan and Xavier, who will be joining me, Ryan, Kristi and Meg for the next leg of our journey. The plan is to sail across the Atlantic with 6 of us on board.

The boat we’ve living on is a Fountaine-Pajot Helia 44 catamaran called Cheeky Monkey, which we’ve owned for just a few months now. Previously, we lived on a 1986 Catalina 34 sailboat, which we sailed from New York City to the Caribbean. Our old boat, Hideaway, is currently up for sale in Sint Maarten, so if you know anyone looking for a boat at a good price, let me know! Here is a write-up on Hideaway: http://turftosurf.com/catalina-34-sailboat-for-sale/


8. Tasha out for a run in the Bahamas 2013




12. Tasha in Ubud Bali with fast WiFi

12. Tasha's work station in Bali

14. Christmas decorations are up on Cheeky Monkey


17. home is where friends are

19. Cheeky Monkey leaving Rabat Morocco

Cheeky Monkey view from above


Tell us your favorite and least favorite room in your space and why?
My favorite room on Cheeky Monkey is the outdoor cockpit space. It’s wide and spacious with a lovely and large teak wood table that seats 10 for dinner or parties. It’s great for drinking cocktails while playing card games with friends at anchor, and it’s also a great space with a view when I’m at sea either relaxing, writing or editing videos for our You Tube Channel: https://www.youtube.com/chasethestoryaroundtheworld

What is the biggest misconception you had about your current living situation before you started living in it?
One of the biggest arguments Ryan and I had in the early stages of dating happened when Ryan told me he had a dream to sail around the world one day. My knee-jerk reaction, being from a small, landlocked town in Upstate New York and having no experience on boats, was to say, “You’re out of your mind. There’s no way I’m ever going to live on a boat.

And Ryan was like, “I’ve just told you my life’s dream and that’s your reaction?!” I suppose at the time, he was thinking how unsupportive I was being. But all I could think about was that book “The Perfect Storm,” and I imagined living on a boat and being constantly thrown about in treacherous seas while loved ones at home fretted and wrung their hands anxiously because they knew it was only a matter of time before I died.

I had a very strong desire NOT to die.

Luckily, I’ve learned a thing or two since then. And I know life at sea isn’t really like “The Perfect Storm.” Thank heavens.

What is the one household item you carry with you every time you move or the one item you cannot live without?
A good corkscrew. I like my wine.

What do you miss most about permanent, stationary, traditional living?
I guess I miss having a routine and the freedom to run, bike and explore land to my heart’s content. When we’re at sea, I find creative ways to keep physically active in such a confined space.

But when we pull into port, the first thing I do is lace up my sneakers and go for a long run. I love biking, running, Cross-fit, skiing, roller-skating and almost any physical activity I can find on land.

On a boat, it takes a lot more organization to keep up a physical routine. In fact, it’s not much of a routine — you just have to take advantage of whatever opportunities there are to be physical. When we pulled into Mallorca, I Googled Crossfit boxes and found FreeMove Fitness and went to classes almost every day while we were in port. I also ran to and from my Crossfit classes.

I basically try my best to cram in as much physical activity as I can between boat projects while we’re on land because I know we’ll be at sea again soon enough and it won’t be so easy to find ways to workout as intensely.

Do you have a pet joining you in this journey? If so, has this been complicated? Any advice?
We have two cats, Charlie and Celia, who lived with us on board our old boat and sailed with us from New York to the Caribbean. We love our cats and wish they were with us on Cheeky Monkey now, but at the moment they are living with my very generous mother because we have struggled to get them imported into Europe, a continent with very strict pet import regulations.

Charlie actually has a Spanish Pet Passport because she’s so well-traveled. I picked her up as a stray in Doha, Qatar, before I met Ryan, and she moved with us to Spain and then to New York and onward. So she is used to getting her rabies shots for her international health certificate every year and going through security at airports.

However, Europe has made their rules about pet import even more strict lately, and they now require additional documents which need to be certified by the USDA, and this was nearly impossible the last time I tried. So we decided to leave the cats with my mom for another month until we can get to the Caribbean and import them into St. Martin or the US Virgin Islands, which requires much less paperwork and a bit less hassle.

What is your best resource to find items you need for your place?
I wish there were an Ikea in every port because that would make my life so much easier with regard to finding attractive, affordable home items. But I never know what we’re going to find, so I just get what we need in whatever store is available in the country we sail in to.

If you could only have one of the following in your home which one would it be and why?
space, natural light, dishwasher or above average internet.
Above average internet. For SURE. I am a writer, blogger and YouTube vlogger, so I am always trying to track down a fast internet connection, and no matter what I find, it’s never as fast as I would like it to be.

Having said that, I appreciate my time at sea when I am completely disconnected from the online world. It allows me to write and create without distraction. But as soon as I hit land, I am like a junky searching for an internet fix. It’s not a pretty sight…just ask Ryan. As soon as we hit port, I’ve got my running shoes on and I’m out scouring the town for a SIM card and a good data package.

How do you keep traditions alive for your family in your unique living situation?
We just celebrated Thanksgiving with 3 Americans on board Cheeky Monkey. We were at sea for Thanksgiving so we made plans to get all the fixings we needed for Thanksgiving dinner on land so we could celebrate while we were en route to the Canary Islands. It turns out we couldn’t find a turkey in Morocco, so we had to settle for 3 small chickens. But it’s not the turkey, that matters; it’s being in good company.

We try to celebrate holidays however we can, wherever we are, because it’s always nice to bring friends together for a party. And with British, French and American nationals on the boat right now, we can probably find an excuse to celebrate something at least once a week.

How do you decorate for the holidays in your unique (less traditional) home or do you skip it all together?
Decorations take up space on a boat, and we try not to load down the boat with things that don’t get used frequently. Ryan did, however, buy a red Starbucks cup ornament the last time we were in New York. And I bought a small tree and a Christmas banner to go with it, though I was under explicit instructions not to weigh down the boat with useless things. All I can say is, they were very light and very worth it.

What is your favorite part about this lifestyle choice?
The biggest reason I love living on a boat is the feeling of total freedom to go wherever I want, whenever I want; our only limitation is the weather.

Just being on a boat stimulates my imagination – we get somewhere new and I start to imagine sailing further afield to places that are hard to get to without a boat, like the Galapagos or some of the remote islands of the South Pacific. It’s such a privilege to sail into a remote port and drop into another world to explore your surroundings. It’s like having a back-door entrance into a country. When you arrive by plane, you often find yourself traveling by taxi to the tourist center of a country or city and exploring from your hotel. When you arrive by boat, you are often tied up to a dock in a more remote part of the country, which may or may not even have an airport. When you step off the boat and onto the dock, you often find yourself in the heart of a less frequently explored part of the country.

It gives you immediate access to local life, the culture and its people, and it gives you a different perspective on a place than you would otherwise get if you arrived by plane in a crowd of tourists.

Many traveling families subscribe to the “house is not a home” theory. What is home to you?
Home, to me, is wherever I feel connected to a place and to the things that make me happy.

When I think about the places I’ve lived and where I’ve been the happiest, I’d say they had some or all of the following things to offer: it was easy to meet and make new friends, the place is beautiful to look at (the rice paddies of Bali, the old walled city of Sevilla, the surf beaches of the Dominican Republic), I have access to sports, I have time to write and be creative, and eating out is cheap. That last one is important because life is always less stressful when you can enjoy life’s pleasures without breaking the bank.

What makes you love the place you live?
I love this particular boat — the Fountaine-Pajot Helia 44 — because of its modern design, the comfortable living space and the luxuries on board that make life on anchor a little easier or more pleasant, like the watermaker (so we don’t have to schlep water from town to the boat in jugs), a washing machine (so we don’t have to track down a laundromat wherever we go), a fast dinghy (our 25 hp dinghy engine means we can get from the boat to civilization pretty quickly) and an espresso machine (because who doesn’t love good coffee?).

Words of wisdom to anyone considering venturing out into the world of unique, less traditional homes?
People choose to live in all kinds of unique, non-traditional ways, according to the lifestyle they want to have. I know families that travel around the world in a camper van or on bicycles, or are permanently on the road taking house-sitting gigs in different parts of the world.

If you choose to live on a boat, it’s because you want to see a different side of the world than you could see traveling with a backpack or arriving to countries by plane.

But to live on a boat, you have to learn to give up fixed schedules and go where the wind and weather will allow. You have to be flexible and open to changing course as circumstances come up — you can’t be bullheaded about wanting to beat into the wind to get somewhere specific when the weather won’t allow you to go or to arrive safely.

You also have to be extremely self-sufficient and learn to work well as a team on board. When you have a problem at sea, like your engine breaks down or something mechanical fails, there is no one to call to fix it for you. You have to put your heads together and figure out how to fix it on your own. It can be stressful to have things break down at sea, but with every new problem, you find a solution — you have to, as you have no other choice — and through the process or finding solutions, you build the confidence to deal with anything that could possible come your way.

Anything else you would like offer?
We don’t have children yet. But we are planning to have children soon. Both Ryan and I are teachers and educators by trade, so we feel confident that both our skills, combined with the education that comes from the lifestyle we lead, will help us raise inquisitive, adventurous, independent children. We know lots of children who live on boats with their parents as they sail around the world and they are some of the most well-educated, savvy children I’ve ever met.

How do you make a living?
I traveled the world with just a backpack for many years, supporting myself by teaching English as a second language. When I met my husband, we moved to Spain so I could get my Cambridge DELTA (Diploma in English Language Teaching to Adults) in Barcelona and then later we moved to New York City so I could do my Master’s degree at Columbia University Teachers College.

It was when we moved to New York that we saw an opportunity to open our own ESL teacher training school called Teaching House. We started with one course in New York, which grew into 30 courses a year in NYC. Then we expanded and opened Cambridge CELTA (TEFL) courses in 14 cities across the U.S. along with 2 English language schools in New York and Boston.

We ran our schools for 8 years and loved every minute of that adventure, but being tied to New York City permanently became hard for us.

In 2008 we had bought a small sailboat and taught ourselves how to sail in and around New York harbor during the years we ran our companies as a way of relaxing and getting away from our work on the weekends.

Eventually, we started discussing the idea of sailing out of New York without stopping and cruising around the world. We started first by sailing to the Bahamas and then the Caribbean. Then we joined the Clipper Round the World Race for two legs, racing from London to Rio de Janeiro, Brazil, and then Cape Town, South Africa to Albany, Australia.

After that, we felt we had the confidence we needed to venture out on our own to sail across oceans.

That’s when we started shopping for our next boat, the one that would take us around the world. And at the same time, we made the decision to sell our businesses in the U.S. so we could sail away without any ties to New York. We sold our businesses in February 2015 and we put down a deposit on Cheeky Monkey in April. In July, we moved on to Cheeky Monkey in La Rochelle, France and we started to prepare the boat for sailing around the world.

It was a life traveling and teaching English abroad that allowed us to build the expertise we needed to turn that profession into a business. And when we sold the businesses, we had the means to take off, to sail off into the horizon. And that is exactly what we are doing now.

As for work now that we’ve sold our businesses? We’re now involved in more creative projects that incorporate our lifestyle. My passion is writing and I’m working on building up a career in freelance writing. We’re also producing YouTube videos and collaborating with crew we’ve brought on board to produce work for our YouTube Channel, Chase the Story.

The idea is to eventually bring in enough revenue from YouTube to bring on crew who have a passion for sailing and being creative and the revenue from the channel will pay for the cost of the crew — their food and living expenses — so they can experience a different kind of lifestyle and use that experience to go on and do other creative and exciting things with their lives.

Quote to Ponder
The biggest reason I love living on a boat is the feeling of total freedom to go wherever I want, whenever I want; our only limitation is the weather. ~ Tasha

If you want to connect with Tasha & Ryan you can find them at Turf to Surf.

WOW! WOW! WOW! I’m madly in love with another traveling family. I am sure you can see why after reading that post. Impressive! So tell me, are you inspired? What are you going to start thinking about changing in your life?

I hope you have enjoyed another post about families living in less traditional homes. See you back here next Wednesday for another amazing family.

Go adventure,


3 thoughts on “Inside A Traveler’s Walls: Tasha & Ryan

  1. Wow-that is quite some résumé you guys have. I actually came across Tasha and Ryan a few years back when I was looking at doing TEFL, but I didn’t realise it was them until I got to the Teaching House bit. I was scribbling a mind map whilst I was reading this and wrote TEFL as a stream of income. Really great story and very inspiring-you interested in their boat Jess? 😉

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