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Got the winter blues? Learn to sail during this action-packed Caribbean vacation

Spend a week at sea with warm breezes, white-sand beaches, and tight living quarters.

Virgin Island Sailing School’s catamaran “Silver Lining” moored in Cane Garden Bay in Tortola.River jordan

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Like many New Englanders, my brother, Scott Young, starts feeling a little bleak at this time of year, as winter’s doldrums snuff out the last sparks of holiday cheer. But one thing can reliably ward off midwinter melancholy. Ask him about sailing the Caribbean, and his face lights up like a sunrise over turquoise seas.

“It’s pure bliss,” Scott says. He and his wife, Helen Young, along with their two kids, have taken about a half dozen sailing vacations in the Virgin Islands over the past decade. They charter a private sailboat — “bareboating,” it’s called — and live onboard, hopping from cove to cove.


But before they could do any of that, they had to learn how to sail. So Scott and Helen earned their bareboat cruising certification from the American Sailing Association by living aboard a 50-foot sailboat in the Virgin Islands with four other students, learning the ropes from an experienced captain.

They spent two weeks working through the three required courses, learning and practicing techniques and maneuvers, navigation, docking, and safety procedures. There were textbooks and even written tests — not your typical lazy, rum-soaked tropical holiday. But Scott and Helen both enjoyed themselves. “It was 100 percent fun,” he says. “Even the teaching parts were very low-key and relaxed.”

That was almost 20 years ago. Nowadays, many sailing schools pack that level of instruction into a seven-day live-aboard course.

Captain Scott Dempster of Virgin Island Sailing School coiling up a loose line.River jordan

“One of the defining characteristics of ASA is it allows you to get a bareboat certification in one week coming from zero experience, and that’s by far the most popular course, especially in the Caribbean,” says Francis Shiman-Hackett, a broker at Bluenose Yacht Sales in Charlestown who taught sailing in the Caribbean for seven years.


While there’s some overlap between the three courses, it’s still a lot to cover in such a short time — some instructors say too much — so expect an ambitious schedule. “It’s an enjoyable vacation, but it is pretty intense,” Shiman-Hackett says. “To pass the class, there’s no lying on the beach.”

A weeklong learn-to-sail vacation in the Caribbean runs $2,500 or more per person and generally includes meals on the boat, certification fees, instruction, and a private room onboard. Groups of four or more can rent out a whole boat (often at a discount), but couples and singles must be ready to spend a week at sea in fairly tight quarters with strangers. Shiman-Hackett says those conditions more typically build camaraderie than animosity, however. “Luckily, sailing attracts a pretty open-minded bunch of people,” he says.

Scott Dempster of Virgin Island Sailing School says a typical day begins in a new anchorage, sometimes with a quick swim or snorkel before breakfast, followed by book review. “After that we’ll break out the charts and lay out a course to our next destination,” he says. “Along the way, everyone participates. It’s hands on for steering, trimming, tacking . . . we also practice our man-overboard drills, stopping and starting the boat — basically all the maneuvers there are to get you where you need to go or out of trouble.”

Those lessons will come in handy if you charter and captain your own boat later on, which Helen says offers a more intimate way to see the Caribbean than a standard cruise or resort vacation.


“You’re sometimes literally the only person on some gorgeous beach,” she says. “The first time we were there, that really blew my mind. I didn’t know that was even possible in the world, to get to astounding beaches like that and be literally alone.”

While some of the Caribbean is still recovering from the deadly doubleheader of hurricanes Irma and Maria in 2017, touring the islands by sailboat also offers a way to help portions of the local economy without taxing the infrastructure — or risking disappointment.

For one thing, you don’t need to worry about lodging on land at a time when some hotels remain damaged or closed. And some of the area’s biggest draws — clear blue waters, white-sand beaches, and lush tropical landscapes — are perhaps best enjoyed by boat.

“St. John is one of my favorite places,” says Brenton Lochridge, founder of Black Rock Sailing School in Boston, which runs winter sailing courses in the Caribbean. Sparsely populated St. John, one of the US Virgin Islands, is mostly protected parkland, and its harbors looked as stunning as ever on a recent trip, Lochridge says. “Even though the towns that do exist were really damaged, 70 percent of it is a national park, so it still looks gorgeous.”

In the British Virgin Islands, The Baths National Park, a spectacular geological formation of granite boulders rising from the sea at the southern tip of Virgin Gorda, is open to visitors. Famous boating institutions such as the Bitter End Yacht Club on Virgin Gorda and the Willy T floating bar and restaurant, off Norman Island, were destroyed by the storms, but many others remain open, Lochridge says. One is Pirates Bight, a restaurant and bar on Norman Island. “They were minimally affected because of the way the island is shaped, so they’re fully operational,” he says. “That’s a wonderful place.” On Virgin Gorda, the Leverick Bay Resort & Marina has reopened with a full-service restaurant.


Meanwhile, other parts of the Caribbean dodged hurricane season altogether. Grenada, far to the south, was unscathed by the storms and offers its own take on paradise. “I like to say it’s the real Caribbean,” says Chrystal Young of LTD Sailing in Grenada. “It doesn’t have any huge high-rise hotels — not yet, anyway, because Grenada is getting discovered.”

A student with a hand bearing compass. river jordan

LTD tries to balance sailing instruction with fun, she says, working in scenic hikes, a beach barbecue, and snorkeling — including a plunge at the world’s first underwater sculpture park. Classes generally sail north, with a stop at Tyrell Bay on Carriacou, the largest of the Grenadines island chain. “It’s a beautiful, idyllic little anchorage with a marina and some small shops,” she says. They’ll often anchor between Petit St. Vincent, a private island resort that welcomes boaters ashore for dinner or drinks, and Petite Martinique.

Helen says one benefit of bareboating is that it allows you to visit places such as posh resorts that you could never afford otherwise simply by mooring or anchoring nearby. “You can get into a lot of these places at a fraction of the cost you’d pay if you were staying at the resort,” she says. “Then you can splurge for the expensive dinner or just have drinks on shore and soak up the ambience a bit before grilling hot dogs back on the boat.”


Just be sure you eat them before crossing international borders. “We got busted bringing like two hot dogs across, and we were in trouble,” Scott says. “We were stuck there for about an hour while they searched the vessel.” Passports and paperwork are required, and without an experienced captain, a customs inspection can easily capsize your afternoon plans.

The bareboat experience isn’t for everyone — mobility issues or motion sickness might mean a miserable time. And with living quarters that more closely resemble an RV than a high-end hotel, expectations ought to be dialed down. “It’s not luxurious. It’s closer to a camping experience than a luxury vacation,” Helen says.

But Dempster says learn-to-sail vacations attract a wide mix of people, most of them drawn by a sense of adventure. “The people who come down really vary in age and motivation,” he says, including couples, groups of friends, and many beginners. “All they really need to know is that they like being on a boat.”

“It’s truly an adventure,” Scott says, and the steady stream of action, from steering through a 15-minute squall to trying to dock at sunset, can appeal to kids, too. “And at any point, you can just stop and let the kids jump off the back of the boat,” Helen says. “Pop them in a life jacket and they can hop off and snorkel or swim anywhere.”

Adventure aside, what my brother treasures most are the evenings — when a Caribbean cocktail of warm breezes, music, and rum drinks can spark unforgettable family conversations after a day of sailing. “The evenings are idyllic,” he says. “When you’re tied up to a mooring ball by one of these little spots of an island, and you’re in the middle of the Caribbean Sea, unadulterated by vast city lights, the stars are what dreams are made of.”


Students from the Virgin Island Sailing School participate in an impromptu man-overboard drill.scott dempster
Charting a course.river jordan
Chris Rundlett, an owner and founder of LTD Sailing, sails “Dogsmile,” a J/105. The fast, stable boat is good for teaching.LTD sailing

Jon Gorey is a regular contributor to the Globe Magazine. Send comments to Follow us on Twitter @BostonGlobeMag.