scorecardresearch Skip to main content

A sail of one’s own: Catching tradewinds in the British Virgin Islands

With a chartered yacht, you can visit places like Sandy Spit, an islet in the British Virgin Islands. GINA VERCESI FOR THE BOSTON GLOBE

Years ago, before our daughters were born, my husband and I, along with another couple, embarked on the most sublime vacation we’ve taken to date — a weeklong private sailing charter in the British Virgin Islands. Our home for the week was a sleek, 38-foot Lagoon 380 catamaran that set sail from Road Town, Tortola, for a six-night tour around 60 islands, islets, and cays in the Caribbean Sea.

With an instructional skipper on board to man the sails and teach us the ropes, and enough booze to host a small wedding, we hopped from island paradise to island paradise stopping to swim in crystalline Caribbean waters, lounge on silky, white shores, and pop into countless beach bars infused with rum and laid back island vibes. In addition to being an excellent yachtsman, Captain Chris spent the week mixing up mean painkillers — the nutmeg-dusted concoction considered the official cocktail of the BVI — sussing out private snorkeling spots teeming with fish, and taking us to less-traveled anchorages in tiny harbors where we had the sunset all to ourselves.


Since that trip we longed to return to the British Virgin Islands and finally brought our three girls on a mini-version of our previous trip, chartering a day sail with stops at many of the places we visited years earlier. Not yet wanting to commit to a full week on a boat with the kids, this was charter-lite — one day aboard a power catamaran that covered more territory than a sailing vessel could, giving them a dose of yacht life.

The British Virgin Islands are everything you hope for when fantasizing about an escape to a tropical paradise. Endless stretches of powder white sand contrasts endless, ultramarine stretches of Caribbean Sea. Palm dotted shores, mellow bars with salty, permanently bronzed expats and free flowing rum punch, where wearing a T-shirt over your bathing suit and donning a pair of flip flops equates to dressing up.


According to Ian Pedersen, marketing manager of the Moorings in Tortola, chartering a crewed yacht is akin to living “ ‘Lifestyles of the Rich and Famous’ without actually being, in fact, either rich or famous.” Chartering a crewed yacht, complete with a chef who greets you each morning with fresh coffee and a gourmet meal at dinnertime, can be surprisingly affordable, especially if you travel during the off-season or with others with whom you can split the bill.

The BVI abound with secluded beaches and hidden anchorages, and discovering your own private slices of paradise remains one of the greatest pleasures of chartering. Here are a few favorites to get you started.

Norman Island and the Indians

Thought to be the locales that inspired Robert Lewis Stevenson’s Treasure Island, Norman Island, right across Sir Francis Drake Channel from Tortola, is a traditional first day sail for boaters. Snorkeling in and around the island’s famed Caves, where Long John Silver supposedly left “15 men on the Dead Man’s Chest,” feels like swimming in a giant aquarium with a kaleidoscope of colorful corals and tropical fish. Nearby, spectacular reef surrounding towering rock pinnacles called The Indians is equally rewarding. Lunch aboard the William Thorton II, a replica of a 1935 topsail schooner nicknamed the Willy T and located in the southeast corner of the Bight makes a great post snorkel pit stop, but the schooner’s nighttime party scene — think body shots and naked leaps into the sea — is the stuff of legend.


Cooper Island

A prime mooring, the palm-fringed paradise of Manchioneel Bay is one of BVI’s most picturesque, and a day spent snorkeling the island’s U-shaped reef — sea turtles are frequent visitors — and chilling at the fabulous Cooper Island Beach Club is vacation at its best. Cistern Point is another great Cooper Island snorkeling spot, packed with brilliant corals and schools of day-glo tropical fish. Nearby, divers in your crew will relish the chance to explore the wreck of the Royal Mail Steamship Rhone, which sunk in a hurricane in 1867.

Virgin Gorda

An overnight anchorage at Cooper Island allows early birds to score one of the National Park mooring balls at the Baths — busier periods often see all of them occupied as soon as nine in the morning. Once ashore, explore the labyrinth of pools and caves created by a remarkable collection of towering granite boulders, some as big as a house. Make your way to the Devil’s Bay Trail where you’ll crawl, wade, and climb your way through stone grottos lit by shafts of sunlight shining through the spaces in the boulders to the pristine beach at the other end. Afterward, treat yourself to a cold rum punch, a dip in the freshwater pool, and fabulous views at Top of the Baths.

Spend the night at the Bitter End Yacht Club on Virgin Gorda’s North Sound, a large, protected bay surrounded by islets and reefs. If you’re overdue for a real shower and a dose of semi-civilization, this is the place to find both.



Located 13-miles north of North Sound and christened the Drowned Island by the Spanish, the highest point on Anegada rises only 28 feet above sea level. Unlike its mountainous, volcanic neighbors, Anegada is an all-coral atoll, which gives it some of the Caribbean’s most sublime beaches and one of the world’s largest reef systems. Armed only with your snorkel, fins, and a few bucks to spend on conch fritters and painkillers, stroll in solitude along swaths of powder white sand at Pomato Point, Cow Wreck Beach, and Loblolly Bay. Evening should find you ordering up succulent Caribbean lobsters fired up in split oil drum grills under the stars.

Jost Van Dyke

The sail from Anegada to Jost Van Dyke is likely the longest you’ll have during your charter, but stops along the way at Guana Island for incredible snorkeling at Monkey Point and indulging in castaway fantasies at Sandy Spit, helps break it up.

Home to the legendary Soggy Dollar Bar, named such because visitors are required to swim ashore, White Bay on Jost Van Dyke has the ability to make anyone decide to throw it all away and become a beach bum. An afternoon spent lounging in a hammock, drinking painkillers at the place where they’re proclaimed to originate, and playing tiki toss attached to a windswept palm equates to bona fide Caribbean bliss. Grab a mooring ball around the bend to the east at Little Harbor in time for the all-you-can-eat barbecue at Sidney’s Peace and Love, where your captain will dine for free.


Cane Garden Bay

Lead parrot head Jimmy Buffet once sang, “I hear it gets better, that’s what they say, as soon as we sail on to Cane Garden Bay.” Though better is a relative term considering your surroundings, you’ll have no trouble ending your charter with a party and a sublime Caribbean sunset at Cane Garden Bay. Spend part of your time here paying homage to the rum you’ve been enjoying with a tour and tasting at the Callwood Rum Distillery, the only continuously working distillery in the BVI. Back on the beach, you can hop from one laid back bar to the next, favorites include Myett’s, Paradise Bar and Grill, and Tony’s Welcome Bar, most of which offer loungers right on the shore. Make sure to find your way back to Quito’s Gazebo, an island landmark owned by big-hearted musician Quito Rhymer, who performs both solo and with his band several nights each week.

Gina Vercesi can be reached at