It’s a recent Monday, early afternoon, on the island of Jost Van Dyke in the British Virgin Islands though when you’re vacationing on Caribbean time, the day of the week soon becomes irrelevant. Sailboats with names like Prodigious (she’s a luxurious, 58-foot sailing catamaran with all the bells and whistles) and Poseidon’s Pearl offload barefooted passengers by dinghy on the sandy shores to stroll to iconic beach bars like Foxy’s and Soggy Dollar, where the classic BVI cocktail, the Painkiller, awaits.
Many beachgoers have arrived on their own after renting a bareboat (sailing speak for a boat that you crew and captain by yourself) to explore this close-together string of 50 islands and cays surrounded by turquoise seas. Other lucky people are traveling aboard crewed yachts, where a guest’s every whim—from a grilled lobster dinner to some wake boarding or tubing before lunch—is the captain and crew’s command.
And the good news is that you don’t have to be a salty dog captain or a millionaire to get a taste of the yachting lifestyle here.
“If there was a boat for us, we were coming,” says Frances Gulick of Dallas, at The Moorings marina in Tortola, getting ready to set sail on a bareboat charter, “The best way to help after last year’s hurricane is to come back and put money into the economy, and we’d heard great things about sailing the BVI.”
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Gulick, her husband, and several friends booked their sailing vacation with the company, which operates the largest charter fleet in the BVI, before Hurricane Irma hit the islands in September 2017. While The Moorings lost 75 percent of its boats in the storm, the company was impressively back up and running in December, just three months later.
Today, The Moorings, one of several sailing charter companies operating in the BVI, has over 150 yachts available for charter, ranging from sailboats and power catamarans to all-inclusive crewed yachts that can accommodate up to ten guests. New boats are being added to the fleet on a regular basis, with roughly 300 yachts expected to round out the inventory by the end of the year.
While no certification is required if you want to rent a bareboat with The Moorings and most of the other companies operating in the BVI, an understanding of basic seamanship, boat handling, and navigation is a must (online applications that will suggest the best boat for you based, in part, on your nautical skills). For crewed yachts, of course, all you have to do is step onboard, kick back, and all the logistics will be taken care of.
“The British Virgin Islands are easy, line-of-sight sailing, and pretty much anyone can do it because you can always see your next destination,” says Moorings captain Martin Street.
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And those destinations are beautiful, indeed, with rolling islands, fish-filled reefs and toes-in-the-sand restaurants to explore as you island hop a loose itinerary that takes you roundtrip from Tortola to spots like Virgin Gorda (where you’ll find the BVI’s most famous landmark, the Baths), Norman Island, Anegada, and Jost Van Dyke.
While The Moorings caters to a more luxury-seeking crowd, with its high-end catamarans and crewed boats, Sunsail is another popular company specializing in bareboat sailing vacations. The company appeals to a more hardcore sailing crowd, with everything from 51-foot monohulls with 11 berths and 38-foot sailboats for more intimate cruising available.
If you’d rather not deal with sails, the best option for you and your entourage might be a power catamaran, which allows you to island hop at a quicker pace and offers lots of room to spread out aboard. You can captain a power cat yourself or go for a crewed version, and both The Moorings and MarineMax, yet another Tortola charter company, have options that can accommodate up to 12 guests.
In addition to the fees to hire your boat and crew, plan to budget extra for moorings fees to overnight in harbors, meals ashore, and tips for the crew (ten percent is the norm). Charter companies can help with provisioning the boat for you in advance with your favorite food and drinks, so you’re ready to toss off the lines and set sail as soon as you arrive. And there are local supermarkets, too, should you prefer to stock up on your own.
When it comes to the experience of sailing the BVI, it is, as they say, priceless.
“The British Virgin Islands offer a tried and true formula for a sailing vacation that people just love,” says Captain Street, who has sailed all over the world, “It’s a good time with a beautiful backdrop, and it’s affordable. You can get a taste of the yachting life at its best here.”
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