My love of stories drives me to write. My love of adrenaline drives me to chase adventures. These two things, stirred together, have dished up this travel and sailing blog aimed at bringing you tales spun from dusty roads and unforgiving seas.

I started this little blog in September 2012, just before I decided to test what I had learned in the five years since I’d started fumbling around on my first boat, a 1986 Catalina 34 called Hideaway.  The plan was to sail out of New York City (with my then-husband, Ryan) and see just how far we could get while also balancing our working lives on the move. As owners of our own companies in the U.S., we were not exactly free to sail away from all our obligations, though we sure as hell tried.

This blog became an outlet for me to tell the stories of my travels on a boat and to connect with sailors, travelers, dreamers and a tribe of wanderers who, like me, were working their way around the world seeking out adventures and shunning stability.

But, before I tell you all those stories, let me introduce myself…


My name is Tasha, which is not short for Natasha, but is, in fact, the 5th most popular name for female dogs in the United States.

My first solo jaunt abroad took me to London, England for a college semester, and I can’t be sure if it was the constant rain, the knee-weakening accents or the thrill of being out on my own, but the experience lit a flame under me, and a life-long obsession with travel was born.

As soon as I graduated from college in upstate New York (St. Lawrence University), I joined the U.S. Peace Corps to teach English in the Russian Far East. In case you aren’t clear on where that is, you’ll see I’ve circled the turd-like landmass that hangs off the ass-end of Russia somewhere between Japan, China and North Korea. Somewhere roughly in that circle is a town called Nakhodka (“a little find” in Russian), which I called home for two amazing years (amazingly cold, amazingly educational).


Once I was released from the iron grip of the former Soviet Union with my Peace Corps readjustment allowance in hand, I was encouraged to ease back into “normal” life in the U.S. and go about finding myself a “real” job. But my life had changed so indescribably that the only thing I knew for sure was I didn’t want to go home and I definitely didn’t want to work in a cubicle. So I spent the next several months traveling around Siberia wondering where all the other travelers were (Thailand, it turns out).

After Siberia, traveling just got easier, so I kept moving and hoping I’d never have to stop. With a sturdy backpack and $6,000 in cash, I found myself trekking through the Baltics, Central Asia, Eastern Europe, the Caucasus and Turkey, living cheap, camping in the woods and bouncing between hostels.

Realizing my money wouldn’t last forever, I returned to England (still raining), worked on a fish farm (hey, it wasn’t a cubicle), got my CELTA TEFL certification and started looking for teaching jobs abroad. Which, it turns out, there are plenty of.

Using the time between teaching posts to continue traveling, I jetted around the Middle East, drove through the villages of Southern Spain and Portugal, hung out on the beaches of South Asia, snorkeled in the Red Sea, backpacked through Central America and drank a few too many caipirinhas in Brazil.

Before long, I started to realize teaching wasn’t just a means to travel. It had become a passion in its own right. And it had the phenomenal perk of taking me anywhere in the world I wanted to go. So I rode that wave to the deserts of Qatar, where I met my ex-husband Ryan, to sleepy Andalucia in southern Spain and to New York City to study English education at Columbia University. Which, for all the hard work it required, felt more like a hobby alongside my day job teaching immigrant kids at a rough international school in the Bronx. Literally, anything was easy after that, so Ryan and I co-founded a company called Teaching House to help people like us fulfill their dreams of traveling abroad and supporting themselves teaching English. Which then led to me opening my own English language schools, International House New York and International House Boston, for foreign students looking to study English in NYC and Boston.

As fabulous as New York is, I knew it wasn’t going to hold my interest forever, so I kept a look-out for the next adventure on the horizon. As such, I’ve learned to sail (and sailed from New York to the Caribbean), tried my hand (and body) at kiteboarding, signed on to crew for a major ocean race, rode boat waves while wakeboarding and would think nothing of running up the nearest mountain, if only someone would come with me so I wouldn’t get lost.

Eventually, the adventure of building and running my own companies started to be overshadowed by the feeling that I was permanently tethered to New York City and the United States, no matter what I wanted to do next with my life. And after a few years of sailing and living aboard a boat, Ryan and I decided it was time for a new adventure and a new mission.

We wanted to sail around the world and do a full circumnavigation. But that would require buying a different boat and selling the companies we spent eight years turning into a success. Which is exactly what we did. We said good-bye to Hideaway and hello to Cheeky Monkey, our round-the-world adventure-mobile. And with that, a new story began…

…and ended. (See below)



*record scratch* Here is where — prior to May 2018 — you may have read a profile on my former husband and travel companion, Ryan. That partnership ended in May 2017, as we prepared to sail Cheeky Monkey from Apataki to Tahiti, French Polynesia and onward towards Fiji, Australia and beyond.

The original plan was to put Cheeky Monkey back in the water during the 3-week break I had from fertility treatments back in California. I had undergone one round of IVF and only got one viable embryo to freeze, so the doctor recommended I undergo a second round of egg retrieval and fertilization before I implanted any embryos.

Despite the stress surrounding the fertility treatments, and the roller coaster of emotions exacerbated by the hormones I was shooting into my stomach 3 times a day, Ryan and I decided to use the 3 weeks between IVF rounds to go put Cheeky Monkey back in the water and sail her to Tahiti.

We made it through one week of doing boat work together before we had an argument to match the many resentment-filled arguments we’d had over the years. That evening, the night before we set sail from Apataki to Tahiti, Ryan stated his desire for a divorce and for me to get off the boat in Pape’ete.

We sailed for three and a half days in silence, all the way to Tahiti. Once the boat was tied up in Pape’ete, I made my way to the nearest travel agency and bought a one-way plane ticket to Maui. I packed up my things and got a taxi to the airport at 3:00 am. That was the last time I saw Ryan.

So, any stories you read here that include Ryan took place some time during our 12 years of marriage, somewhere on a boat. Just know that relationship is no longer. And I no longer live aboard s/v Cheeky Monkey.

Cheeky Monkey continued sailing without me on board and is currently docked in Sydney, Australia, where arrangements are being made for it be sold by a broker as part of the divorce. If you are interested in buying s/v Cheeky Monkey, please send a message through the contact page on this site.




Cheeky Monkey is a 2015 Fountaine-Pajot Helia 44, which Ryan and I bought when we sold our companies in 2015 and decided it was time to leave North American shores and head off on a journey around the world. As you can see, Cheeky Monkey is quite an upgrade from our previous cruising boat Hideaway (see below) but the increase in liveaboard space was something we wanted not just for us.

I dreamed of sharing this journey with friends, travelers and sailors, so I wanted the kind of liveaboard space that would allow us to spread out comfortably at anchor and also have guests on board without feeling like sardines packed into a floating can. After all, what’s the fun in keeping all this luxury to ourselves? Instead, we thought it would be fun to invite fun, talented, dynamic people on board to share in the adventure and the fun of doing something adventurous (like sailing across oceans) and creative (like making films for Chase the Story, our YouTube Channel).

One of the most commonly asked questions I get about our new boat purchase is “Why this boat? What is it you like about it?”

So I wrote this post Choosing the Right Boat for Us: The Fountaine-Pajot Helia 44 to offer a little insight into my thought process when shopping for our “dream” boat.

And if you’ve found this site because you are interested in buying a Fountaine-Pajot catamaran one day, you may have already read about the hardships and successes we’ve had with our purchasing process — it’s something I’m very open to sharing as there are pitfalls that I wish I’d known better to avoid.

I’m easy to reach via my Contact Page or on Facebook, Instagram or Twitter. Just give me a shout and I’d be happy to have a conversation about my experiences buying a new boat.



hideaway sailing around the world travel blog

Hideaway was my first boat and the boat I sailed with Ryan when this blog started.

She is a Catalina 34 coastal cruising sailboat named for what we used it as, as well as a bar in TriBeCa, New York, on the corner of Greenwich Street and Duane Street. This adorable neighborhood pub is where Ryan first got our friend Rich drunk and convinced him to buy a boat with us in 2007. The rest is, well, a story that has resulted in a lot of blog posts.

For all you curious boat-lovers out there, here are a few photos of my former floating home:

hideaway catalina 34 interior

We chose Hideaway for her roomy, comfy interior space.

hideaway catalina 34 highborne cay bahamas

Kitted out with all our toys and docked at Highborne Cay Marina, Bahamas.