How Three Families Quit Real Life to Live on a Boat (And Get Paid for It)

And how you can do it, too

March 24, 2021 5:39 am
The Dauntless
The Dauntless
Javierto Mar

Various and sundry are the stories born from the pandemic of people who traded in their former lives for newer, more adventurous ones. We just wrote about the rise of #boatlife — more or less a seafaring version of the more ballyhooed #vanlife craze currently taking over America’s most coveted outdoor playgrounds — and it’s possible that it’s led to some inner dialogue on your end.

Could you, too, pack life as you know it onto a boat and travel full time, all while working and possibly raising a family? Maybe. But it’s probably something you should take for a test drive first.

Fortunately, those people who are already doing it are a lot savvier than we are, and many of them have already turned their boats into charter vessels or the vehicles for lucrative side gigs as travel guides, sailing instructors and internet personalities. For neophytes, these sailing influencers are an invaluable resource: before splurging on a boat that you (probably) have no idea how to operate, check out their content to learn more about what it entails — or literally book a stay on their boat, since some of them offer that.

Below, meet three such operators, from one of YouTube’s resident sailing couples to a pair of families that host charters and group trips around the globe.

Sailing Ruby Rose

About the crew: Twelve years ago, Terysa Vanderloo and Nick Fabbri met in India. About a year later, Vanderloo left Australia, and together, she and Fabbri settled in the U.K. Fabbri was a part-time sailor at the time, having tooled around in a remote area of the U.K. on the weekends.

“I didn’t realize, and I don’t even know if Nick realized, that people out there lived on their boats. That, to us, was a very novel concept,” Vanderloo says. “We were aware that there was this community out there of what we call live-aboard sailors or live-aboard cruises, but we didn’t know much about them, or what they did, and how they did what they did, except that it sounded really cool. We started doing some research, and we realized that that was something that we could actually do ourselves.”

So they put a plan in place, began renting their flat in London for some added income and eventually traded in their weekend sailing boat for a new Southerly 38. They named her Ruby Rose. Fast forward to 2021, and Vanderloo and Fabbri now have six years of sailing experience, more than 25,000 nautical miles and two trips across the Atlantic under their belts to go with 130,000 social-media followers worldwide.

What they do: Vanderloo and Fabbri run the number-one sailing YouTube channel in Australia and the U.K., titled Sailing Ruby Rose. Born of a blog Vanderloo kept during their first sail across the Atlantic, the channel essentially produces two simltaneous programs: one revolving around day-to-day life on the boat, the other an educational series for new sailors and boat enthusiasts.

“We pick a topic and we do a video specifically on that topic, and it can be anything from how to install a solar panel, service your outboard engine for your dinghy — or your inboard engines for that matter — to how to actually sail and set your sails,” Vanderloo says.

“People watch [our] YouTube videos, [and they get] inspired,” she continues. “But we also try really, really hard to match that inspiration with education, practical information and a dose of realism. This is what it is like to live on a boat, and this is what you need to do.”

Most recently, Sailing Ruby Rose’s followers have been treated to front-row seats of Vanderloo and Fabbri designing and building a custom boat from the ground up in partnership with an Australian catamaran manufacturer. Ruby Rose II has introduced a new, third element to their channel that has proven wildly popular — a testament to the ever-increasing interest in sailing.

“We announced a new boat in July of 2020, so about eight months ago. It just went insane, like literally,” Fabbri says. “[The catamaran manufacturer] expected to sell 12 boats in the first 18 months, from July until Christmas this year, and they sold 40 boats in the first three months. You cannot buy one of these boats until 2026 now. They hold no stock of any of the models.”

Over the course of the next few months, Fabbri and Vanderloo will be sailing catamarans along the New South Wales coastline and the Whitsunday Islands while they wait on the completion of Ruby Rose II — all of which you can bear witness to on their channel.

Their advice for you: “If this is something you want to do, don’t rush into it, take small steps. If you’re learning to, say, ski, your first day on the ski slopes is not going down a double-black-diamond run, tearing the ass out of it, and hurting yourself and scaring yourself, because it just puts you off,” Fabbri says. “You do things slowly under the tutelage of more experienced people, either instructors in sailing schools, or experienced skippers. That is a really good way of filling you with confidence and making sure that you end up loving what you’re doing.”

The Dauntless
The Dauntless
Javierto Mar

Sail Dauntless

About the crew: In another life, Jim and Judy Brown were landscape architects living in Western Loudoun County, Virginia, in a house they designed themselves. “We had a beautiful view, it was a beautiful place — a great place to raise the kids,” Judy says. “Then we said, ‘OK, we’re ready for the next thing, they’re grown, they’re independent, what can we do next?’ We both love water, we’ve been sailing on and off since we’ve been teenagers, and we’re kind of landlocked in our place in Virginia.”

Because they had once served as their own general contractors, they had 20 years of equity saved up on their property, which eventually became the down payment for the purchase of a boat.

“I had no idea what we would be doing after our corporate career [when we built that house],” Jim says. “It’s kind of funny how everything comes around.”

The Brown’s bought their boat, and after five years of research and development — and while they still had, as Jim puts it, their “strength and sanity” — they left their jobs and moved onboard.

What they do: The Brown’s run a charter business, Sail Dauntless, which before COVID could typically be found around the Caribbean, with guests hailing from all over the world. According to Judy, the planning portion of the trips they host generally begins anywhere from a year to six months in advance of departure. Included in that planning is a preference sheet in which guests are invited to discuss activities they’re interested in, places they want to see, food they enjoy, the amount of activity they’re looking for, etc. From there, the route is customized to their preferences. Then, when the time comes, guests are picked up directly from the airport and transported to the Dauntless, where their Skipper, Jim, and First Mate and personal chef, Judy, await their arrival.

Of course, COVID has forced them to pivot a bit — a not altogether awful prospect for the Dauntless crew, according to Jim. “One nice thing about being travelers and adventurers is [we can ask ourselves], ‘OK, so where do we want to go?’ It is that simple,” he says.

Sail Dauntless is now taking reservations for one-day, two-day and weeklong charters in and around Sag Harbor, namely the Hamptons and Newport.

Their advice for you: “A lot of people are buying boats because they feel like, ‘Well, this is the thing to do now,’ Jim says. “What we want to caution is that you can’t just go out and buy a boat and have a good time. You have to get some experience or put some people with experience on your boat that you’ve purchased.”

“I expect to see and hear about a lot of boating accidents this summer from all these folks who have had the money, and gone out to buy a yacht and said, ‘I’m going boating,’” he continues.

Luckily, there are alternatives to purchasing a yacht straight out of the gate — charters, chief among them.

“One of the other things we offer is the try ‘before you buy,’” Judy says. “[Guests can] come check us out, stay with us for a week, we’ll show whatever they want to learn so they can see how it all works, and if they even like the way it feels [before they go out and buy their own boat].”

The Sueiro family
The Sueiro family

World Towning

About the crew: Jessica and Will Sueiro have been traveling full time with their two children for the past seven years. “We love to travel, but the main reason was we wanted [the kids] to explore the world and learn and be educated out in the world,” Jessica says. “We wanted them to gather experiences rather than stuff, create memories, and we wanted to be closer as a family, and travel kind of ticked all those boxes.”

They kicked things off with a year in Costa Rica, followed by nine months in Ecuador and, after that, another 10 months in the South of France. By the time they’d reached France, after almost three years of full time travel, they were ready to shift gears again. The kids pushed for an RV.

The RV signified the next chapter, in which the Sueiro family would go on to visit every country in Europe. “After that, we decided we really wanted to explore Asia,” says Jessica. Shortly after arriving in Asia, however, COVID began to ramp up and the Sueiros wound up spending almost six months locked down in an otherwise touristless Japan. Eventually, their visas would run out and they’d face a decision: What next? 

Soon, Jessica stumbled across an ad for a boat on Facebook. “We decided that the project would not be necessarily remodeling a house, but learning how to live on a boat and learning how to sail while in lockdown in France,” Jessica says.

Moving onboard during COVID was hardly a fairy tale. The Sueiro family was confined almost exclusively to a marina in the South of France for the entirety of winter. Though years of travel experience left them uniquely positioned to take on many of the challenges of boat life, they had no previous sailing experience, and learning in the midst of a global pandemic was a tall task. But finally, after six stagnant months, the Sueiros set sail for the first time last week. 

What they do: Jessica and Will currently sit at the helm of WorldTowning Voyages, a family-owned, full-time travel consultancy that specializes in “deeper connections to off-the-beaten path experiences and intense engagement with locals.” It’s their mission to educate others on the trials and tribulations of full-time travel, and in particular ventures like buying and moving onboard a boat. And what better way for potential full-time travelers to test the waters than by living alongside some seasoned ones?

“Will and I, our goal has always been to share this lifestyle, the good, the bad and the ugly, so that other people can see the realities of it and see if it is for them,” Jessica says. “It really is not for everyone, and I’m not just talking about sailing. I’m talking about just travel in general. The more you can get your hands on stuff that shows the realities of it to kind of remove the rose-colored glasses that social media predominantly shows us, the better off you’re going to be, and see if this is really for you.”

WorldTowning has just recently opened up their first group trip of 2021 to Morocco, for which they are now accepting reservations. In 2022, group trips will expand to include Costa Rica, Ecuador, Peru, France and India.

Their advice for you: “Don’t do it because it’s cool. It is a lot of work and there’s a huge learning curve. Start educating yourself now,” Jessica says. “Even if you’re not buying the boat for two years, start the education process now. This is not like van life. This is not like going and traveling around Europe with a backpack. This is not like going to just live in a foreign country.”

That said, according to Will, the payoff is certainly worthy of the investment.

“You have to be really, really, really thick-skinned when it comes down to it, and this is not necessarily just [in regards to] the boat,” he says. “It’s about making choices that are unconventional. You really have to want it more than life itself. If that is the case, if you really want it more than life itself then, without getting all new-agey, the universe finds a way. You will find a way to make it work out.”


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