Blogger Interviews: Sailing Stories Pt. 3

Philipines Zizoo

Want to hear from one of our favourite travel bloggers? Check out this interview!

We’ve obviously got big love for sailing holidays.

The feeling of escaping everyday life for crystal clear seas, secluded beaches and stunning coastal towns is our perfect holiday.

That’s why we do what we do, here at Zizoo.

But we’re fascinated by the people who take this love and turn it into a full-time obsession.

Life on a sailing boat is an intriguing one, so we’re bringing you a series of interviews with our favourite sailing and travel bloggers, to show you what it’s like.

This month, we speak to Tasha from one of our favourite blogs, Turf to Surf.

Read the full interview below!

girl on beach sailing holiday Zizoo


1. What sparked your passion for sailing, and what made you decide to adopt sailing as a lifestyle?

I’d have to say it was less of a ‘spark’ and more of a grenade that got dropped in my lap.

Sailing was never on my radar until I met my husband. It was something he talked about incessantly as a far-off dream when we first started dating. But I never took it seriously or as anything that would become even a small part of my life. I just assumed when Ryan talked about sailing it was like someone saying, “If I won the lottery, I would [fill in the blank]”. Like, “If I won the lottery, I’d buy my own island in the Caribbean,” or “If I won the lottery, I’d quit my job and sail around the world.”

When Ryan said, “I have this dream to sail around the world one day,” I laughed hard. Really hard. I probably even snorted. And Ryan got really offended because, in his words, I was laughing at his dream.

We were travelers before we ever met each other, and we were used to hopping from country to country teaching English for whatever money we could make to keep traveling. When I met Ryan, I was teaching in Doha, Qatar for good money. And then we moved to Seville, Spain together, where I spent a chunk of my savings on doing a diploma-level teacher training course. Then I got a job that paid 1000 euros a month in Seville, but I had to pay our entire 525-euro-a-month rent because Ryan’s meager salary went entirely to paying off his UK student loans. So when I say there was no money to buy a boat, I mean there was barely enough money to pay the rent at the end of each month.

At the end of every month in Spain, we’d raid our collective coin jar to buy things like milk and wine… you know, the essentials. The whole idea that we would have enough money to buy a boat one day was laughable. But then again I also thought at the time that only millionaires could afford boats. It never occurred to me that boats are much cheaper to buy than most city apartments.

Of course, that depends on the boat you go for. I’ve met guys who’ve rocked up in the Caribbean on a $5,000 24-foot boat they sailed from Canada. And I’ve met retirees sailing around on boats worth hundreds of thousands of dollars. I guess it’s like anything — if you have a dream, the money only matters insofar as how much you have to spend. If you have nothing to spend, you can still go out there and achieve your dreams.


hideaway-sailing holidays in the bahamas Zizoo

2. What kind of boat do you sail, and what’s been the biggest challenge with it?

For the last 7 years, we’ve been sailing on a Catalina 34 called Hideaway. She was our first-ever boat, the boat I learned to sail on and the boat that inspired my desire to keep going farther and farther afield until I could see the next coast or the next island.

The biggest challenge with Hideaway was that she was old. She’s a 1986 boat that we bought in near-perfect condition. Anything that wasn’t perfect on the boat fell apart on us the farther we sailed from New York. The good thing, though, was that through the process of cruising and learning to sail, we learned how to fix just about anything on that boat ourselves. Hideaway was and very much is the perfect live-aboard cruiser and she’s taken us thousands of miles already.


3. What are the 3 things you love most about sailing?

    1. The freedom. You go where you want when you want (so far as visas allow).
    2. The challenge. You learn so much just by being completely self-sufficient. From afar, it looks like cruisers are just knocking back cocktails with views of perfect sunsets. But often what’s happening in between all the gorgeous Instagram shots is we’re up to our necks in grease and we’re swearing our heads off as we try to figure out why the engine’s not working. And the greasy moments far outnumber the Instagram cocktail moments. But I wouldn’t have it any other way.
    3. The adventure. Have you ever run a marathon? Rowed around an island? Done anything you never thought you could do? When you reach a new shore after numerous days / weeks / months at sea with your boat still in tact and all your wits (almost) still about you, that is exactly what it feels like. It feels like an adrenalin rush that’s there to remind you that you are stronger than you think you are. That feeling is AMAZING.

4. Where are your 3 favourite sailing destinations and why?

This is a tough one for me to answer because sailing is not always my motivation — often, there are places that appeal to me because I want to get off the boat and go exploring on land. And there are other places that appeal to me because being out on the water is so amazing.

Truth be told, as much as I love the challenge and adventure of the journey to a place, what I love most is tying my shoelaces, getting off on land and running myself ragged seeing what an island, country or city has to offer. I adore mountains, land, people, cultures, food, bars…getting to those places by boat just makes me appreciate all those things all the more when I finally get there.

Having said that, my favorite places so far on our sailing journeys have been (in no particular order):

  1. The Dominican Republic – Sailing there from the Bahamas was a challenging adventure, but getting off the boat and clambering onto land was an even bigger adventure. In particular, I fell in love with a surfing/kiteboarding town called Cabarete and we decided to delay sailing onwards in order to rent a house near the beach for a few months. During that time, we did some online work (we still owned our own companies at the time), did some water sports, took up Crossfit and basically fell in love with the vibe of Cabarete and the surf-loving Dominicans.
  2. The Virgin Islands – You don’t get much better than the U.S. Virgin Islands and the British Virgin Islands for stress-free, easy-going sailing, punctuated at the end of each day by cocktails and friends in the adorable bays located just a few hours’ sail away from wherever you are. The islands are stunning and remote enough to make you feel like a true explorer, and yet you meet friends on boats wherever you go in the islands. The Virgin Islands are a true sailor’s playground for sailors of all levels of experience.
  3. The Bahamas – there are very few places in the world that can blow you away with the sheer beauty of the water, its color and the sea life in it. I’m sure when we get to the South Pacific or the Philippines we’ll be blown away again. But for sailing in the Americas, I’ve not seen anything as stunning as the water and white sand beaches of the Bahamas.

sailing holidays in the British Virgin Islands Zizoo

5. Which coast has the best: a) sailing conditions? b) food? c) people?

For the kinds of sailing conditions that are good training conditions, I’ve never met such intensely different weather patterns than those off the coast of the UK. But I’m not sure this is what people think of when they say “best” sailing conditions, though I loved it. For sailing conditions like the kind you find in those sunny, dreamy commercials advertising things like Viagra, I would recommend the BVIs. It’s sail-by-sight, the winds are consistently tame and there is so much to see on each island.

The best coast for food that I’ve been to are any of the French islands in the Caribbean. I mean, who can beat French food? Well, unless you’re Thai. I need to sail to Thailand so I can change this answer to THAILAND. I have yet to sail to Asia, so I can’t count any of those islands on my list of best meals I’ve sailed to. But let’s be honest — Asia is killing it when it comes to good food.

The best coast for people? I adore the Dominican Republic. I speak Spanish pretty well, so it’s easy for me to connect with the people, but mostly I’ve found that Dominicans are incredibly hospitable, carefree and outgoing — they love loud music and they’ll come up with any excuse to have a good time. And who doesn’t love a good time?

sailing dominican republic zizoo

6. Would you advise people to try chartering yachts before purchasing their own?

Absolutely! Though I would also advise people to do what most inspires them. Chartering a yacht in a place like the BVIs will open you up to the fun of being in a Caribbean cruiser’s playground. It really is a beautiful and remote part of the world.

It’s true, people often need to take baby steps towards their dreams in order to feel comfortable with the changes they are considering. It might start with a basic sailing course, maybe some weekend crewing, maybe chartering a boat somewhere beautiful, and through all that they can build the confidence to hopefully buy their own boat and start experimenting on their own one day. All that makes perfect sense, as it is an incredibly sensible way of tackling the dream of buying a sailboat and going cruising one day.

Ryan and I don’t really work like that, though. So, I also know there’s another option — cannonball into the deep end with little more than your faith that whatever happens, it will be an adventure. Some might say buying a boat when you have no idea how to sail is a little crazy. But for some people, jumping into the deep end can be very motivating. Or is that just us? Ryan and I bought Hideaway in Connecticut in 2008 and had no idea how to sail it, let alone how to sail the blasted thing back to our home harbor of New York City.

So, what did we do? We hired someone to spend a weekend teaching us how to sail our boat. We may be a tad reckless, but we’re not stupid. We knew we could figure it out eventually, but we also knew we’d need a lot of help along the way.

And where are we now? We’re in La Rochelle, France, having just moved aboard a brand-new Fountaine-Pajot Helia 44 catamaran, which we decided to buy after we sold our companies in February 2015. So here we are. That drastic decision to buy a little sailboat we had no idea how to sail a mere 7 years ago has led to us moving onto a boat that we will spend the next five years sailing around the world on. The whole idea of it is so crazy I sometimes think I’m having an out-of-body experience when I think back to that young woman in Spain who had just started dating Ryan and was like, “WTF?! No one does that, right?!”

7. What’s your favourite sailing quote?

Oh, man. Can anyone beat Mark Twain’s quote?

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

Honestly, this quote spoke to me of adventure and the importance of pushing yourself out of your comfort zone long before I ever discovered sailing.

sailing in Bahamas with Zizoo

If this interview hasn’t inspired you to book a sailing holiday, we don’t know what will!

Tasha’s life is certainly one-of-a-kind, and we hope you’ve been sufficiently inspired to throw off the bowlines, sail away from the harbour and explore, dream and discover on your next sailing holiday with Zizoo.
Rent a boat now!