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The Rise of the Young Yachties

Before I went there, I thought that paradise was reserved for ex-pats and old salts. I thought it was a place you drifted to, eventually, on your sailboat, after the job, the kids and the house were in your wake. 

Before I went there, I thought that paradise was reserved for ex-pats and old salts. I thought it was a place you drifted to, eventually, on your sailboat, after the job, the kids and the house were in your wake. I thought that becoming a cruiser was certainly out of my league and probably out of my price range.

Then, at 26, I hopped a flight to Tonga, found my friends aboard their 41-foot Newport and joined the cruising community as a member of a growing faction: the Young Yachties. I had just lost my government job—a job I had only landed after spending a year as an unemployed college graduate. My friends Geoffrey Oliver (28) and Chris Matthews (28) had recently left Victoria, British Columbia, bound for Hawaii aboard their overhauled Newport 41, One Flew Blue. After surviving the brutal 26-day passage, Geoff called me from Hilo, and without skipping a beat I said, “I want to come with you.” We decided I’d meet them in the Kingdom of Tonga, a remote group of South Pacific islands holding their own between Fiji and Samoa. We’d all heard that Tonga was the real-life paradise.

Within a couple of weeks I was blazing through keelboat lessons at the local marina at Oak Bay, full-speed-ahead planning my trip and packing up my life. As a novice sailor, I didn’t know what to expect, but I was quickly surrounded by the offshore cruising community—and just as quickly made aware that our crew did not fit the mold for the typical cruising demographic. 

This became even more evident after arriving in Vava’u’s Port of Refuge harbor in Tonga, where I received a business card from an anchorage neighbor that read, “Retirement…the way it should be.” A couple of weeks later, following a disoriented book exchange, The Book of Senior Moments turned up in our cockpit. Along the way, we were often mistaken for crew on retirees’ boats. Though we met plenty of young people who were crewing, we met just as many who were captains of their own ship. These were our fellow Young Yachties. 

After cruising the South Pacific for a year and meeting dozens of other Young Yachties, I’ve discovered that “paradise” isn’t only reserved for retirees. It can just as easily be a place in which you can come of age, an experience that can transform you, ignite a desire for social change and inspire action on a global scale. The trick is getting there. 

Bret & Chad van Roden (26)


I met Bret and his twin brother, Chad, in Neiafu, Tonga, when they were a third of the way through a three-year circumnavigation, sailing aboard their schooner Broken Compass. Both had left professional trajectories in the financial sector to try something new. Prior to the trip, the twins had sailed a total of two days between them. Now, they could add island-sitting (yes, it exists), pearl diving, liming and offshore sailing to their resumes. 

In paradise, they learned self-reliance on a scale that’s tough to match. Once, after their boat was looted and all their navigation equipment stolen, they sailed from Panama to Ecuador with nothing more than a compass. Another time, when reeling in a tuna, the treble hook ended up slicing through Chad’s calf and Bret’s quick-thinking and bolt-cutter skills saved him from bad lacerations at sea. How do you fit that in a cover letter?

For these guys, the traditional post-college paradigm—marriage, job, kids, ready, go!—didn’t hold much water. “Feeling fulfilled, finding your passion, and making an impact are higher on the priority list than making a lot of money and following traditional career paths,” Bret says. 

Annie Brett (23)


Annie Brett was the youngest captain we met, and amazingly, in charge of one of the largest boats we cruised with: the 120-foot ketch Infinity, owned by Infinity Expeditions, a nonprofit that promotes global awareness of environmental issues. They volunteer with research projects, beach cleanups, protests, species counts and most recently, a project called “In Fifty Years” that captured environmental perceptions from around the world, particularly in the small islands of the South Pacific. 

In a way, Infinity is a microcosm of all Young Yachties. On board were students in biology and engineering, recent graduates looking for life experience, professionals in search of a fresh start, a divorcee on the run and several free-spirit travelers. Annie herself is a Harvard grad with degrees in environmental science and biological oceanography and a USCG 100-ton Masters License. This eclectic sea-tribe voyaged to remote islands, met their inhabitants and was often invited to take part in the local tribe’s traditions. In doing so, they learned how to handle storms, seasickness, diversity, each other, and all the emotional and mental challenges that come with life offshore. They unplugged and reflected. They saw how humans are tied to the planet and its resources.

Like many Young Yachties, Annie’s cruising filled a window of time. After two years aboard Infinity, Annie started work as the program lead for Sailors for the Sea, an ocean conservation group. This fall, she starts a PhD at the University of Miami’s Abess Center for Ecosystem Science and Policy, focusing on marine conservation.


Jefferson Pereira (24)

“For me, cruising was the first time I could see the Earth as a planet, raw like Mars or Jupiter,” says Jefferson Periera, after spending many days on a passage with nothing but the ocean and the stars. I met Jefferson and his sailing mate, Ana, in Neiafu, Vava’u. At the time their boat required repairs in a mosquito-ridden haulout, so we took them cruising for a few days. 

Instantly, I could tell that Jefferson’s drive was infectious. He shared podcasts of philosophy lectures, taught the guys how to spear fish, gave tips on tow-surfing behind our over-powered dinghy, and even spoke at a local coffee shop about sharks and overfishing. 

His Young-Yachtie story was an inspiring one: after graduation, Jefferson left his native Brazil aboard a 68-foot steel ketch that was teaching sail training to young Brazilians as it cruised through Panama and the Galapagos to the Marquesas. On board, Jefferson met Ana, who was also a recent university graduate, and together they switched boats to crew aboard a retired widower’s monohull from Tahiti, through the South Pacific islands, to Australia. From there, they flew to Bali, where Jefferson spent seven months as first mate aboard a 70-footer, cruising the Maldives and Thailand. 

After this five-year adventure, Jefferson returned to Rio to get his Masters in Oceanic Engineering. Now, as a Young Yachtie living back on shore, Jefferson says he can see how his experiences offshore continue to impact his life, where he actively volunteers with several environmental, sailing and social causes. “We are young,” Jefferson told me, referring to his fellow sailors, “but imagine when we are 40 or 50, when we are leaders. Now we’re sailors, environmental educators—but maybe when we’re older we’ll be senators, politicians, people who can pass laws. And we’ll have this global perspective to draw from.”


Lee Winters (32)

Of all the Young Yachties I met, Lee Winters was the most resilient. When I met Lee in Neiafu, he was sailing under an upside-down mizzen set as a foresail—a creative replacement for his missing forestay and jib, which had fallen overboard between Rarotonga and Tonga. He was also harboring a massive coconut that had landed on his head in Wahine, resulting in an emergency helicopter ride to Papeete. At the time Lee was still trying to decide if he should plant it or do something more destructive to it; he eventually settled on tossing it into the ocean near a palm-tree-populated island to give it a chance at survival. Along the way, he’d also survived reef-fish poisoning at Chesterfield reef and nearly sinking in the Indian Ocean when his propeller shaft came loose from the stuffing box. 

“I kinda learned the hard way,” he says. Like Bret and Chad, Lee hadn’t sailed a single day before deciding he would sail around the world. He had a lucrative career in software sales and decided to leave for a different, more adventurous type of sails. Once inspired, he took a few lessons, bought Jargo, his 38-foot Allied Mistress Mk III, and cast off, sailing solo for an organization called Children’s Villages. 

At this point, the MBA grad doesn’t see himself returning to a life in the office. “I couldn’t imagine going back to the corporate world,” he says. Instead, he’s going back to help on the newly acquired family farm. “I’ll trade my foul weather gear for boots and a John Deere tractor,” he says.

So why the rise of the Young Yachtie?Why now? I believe a host of factors is at work. For one thing, there are more high-quality boats available secondhand than ever before. For another, advances in satellite communications, navigation and safety equipment have made it easier for every demographic to head offshore. Jobs ashore are hard to come by, and even if you land one, there’s less pressure to rush through the usual adult benchmarks and more encouragement to “take your time.” 

So we the 20-somethings cast off lines and head for paradise. And once there, we discover things we’d never have learned on shore. Like Bret and Chad, we learn self-reliance. Like Lee, we learn resilience. Like Annie and the crew of Infinity, we interact with new cultures and experience the ocean up close. Like Jefferson, we become inspired to give back. And like my crew, we discover new skills and then go home to pursue them: Geoff begins Coast Guard College this fall, and Chris is preparing for paramedic training, a calling he discovered after he removed sea urchin spikes from Olivia’s hands and legs, treated his own foot after a run-in with the outboard engine’s propeller, and spearheaded a late-night rescue when a neighbor fell from their mast. 

And that’s the biggest difference between us and the rest of the cruising community: after this, we’ve got our whole careers ahead of us. While cruising, we’re like sponges, soaking up observations and inspirations to apply to the next chapter of our lives: “the real world.” 

That was a topic that came up a lot while in paradise: the job you left, the school you’d graduated from, the town you were born in. Then one day a peer of mine pointed out, “This is the real world,” and she was right. As my crewmate Geoff said, “The real world is the world you see when you’re alone with your thoughts and connected to nature. Back home, that’s not the real world, that’s the world you’ve dumped all sorts of crap on.” This world, without coffee shops, TV, garbage pickup, and high-rises; this world, paired down to people and resources and paradise; this is the real world. And we, the Young Yachties, are the lucky ones who’ve lived in it. 

After her year as a Young Yachtie,

Emily Kennedy returned to Canada

to work as a travel and music writer.

She hopes to get saltier with age

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