Choose Your Own Adventure on a Chartered Sailing Trip Through the BVI

Sparkling waters, fresh breezes, and all the snorkeling and cocktails you could want. Embrace the freedom of sailing through the British Virgin Islands on a private chartered catamaran.

Choose Your Own Adventure on a Chartered Sailing Trip Through the BVI

Eight days on a private, chartered catamaran in the British Virgin Islands might just be the perfect family vacation.

Photo by David LaHuta

“Time to take off those monkey suits and get into your swimming costumes.” The playful request comes courtesy of captain Richard Hallett, a South African by way of Zimbabwe, who along with his wife and first mate Shannon, is crewing the 50-foot Moorings catamaran that my family chartered for a nine-day sail in the British Virgin Islands. We’ve been aboard our yacht for all of one hour when the suggestion is hurled toward our two school-aged sons. Not surprisingly the challenge is met with gusto. So, following a 30-minute sail to Norman Island from Road Town, Tortola (the capital of the BVI, our launch point after flying into its Beef Island Airport), we anchor off a calm bay called Treasure Point and prepare to snorkel inside three water-level caves. Almost immediately we’re met with colorful schools of parrotfish, yellowtail snappers, and striped sergeant majors, plus vibrant clusters of orange cup coral that the boys enjoy snapping pictures of with my underwater camera.

Back onboard we’re given two options by our captain: sundowners at a fancy waterfront restaurant called the Bight or cocktails and cliff jumping at the Willy T, a tanker that’s been turned into a floating dive bar, where you can shoot spirits from six-person “shot-skis” (long wooden snow skis with shallow holes to fit shot glasses). We opt for the latter and take the plunge, what ends up being the first of many on-the-go choices that define the vibe of this kind of vacation. “The beauty of the BVI,” says captain Richard later that night, “is that you can point your boat in any direction and find an amazing experience just a short sail away.”

Indeed, much like the Choose Your Own Adventure books that I adored as a child—the ’80s-era series where you assume the role of the protagonist and make choices to determine the plot’s outcome—so too is this grand sailing holiday that we’ve found ourselves on. If you decide to snorkel on the shipwreck, turn to page 51. If you’d like to sail to the beach bar, turn to page 86. The only difference is, instead of italics at the bottom of each page, our choices come hand-picked from our seasoned captain, whose encyclopedic knowledge of the territory has already proven wildly successful.


Left: Cow Wreck Beach Bar, where we stopped for rum punch. Right: the Baths, a maze of boulders on Virgin Gorda formed by an underwater volcano.

Photos by David LaHuta

The other benefit? Now is the perfect time to charter a yacht in the Caribbean. Thanks largely to the pandemic, the BVI is eerily quiet at the moment, which means you’ll find empty anchorages, secluded snorkel sites, and slices of white-sand beaches that will fulfill your every Tom Hanks Castaway fantasy. Add to that the opening of a handful of brand new (or newly improved) resorts and restaurants throughout the territory and you’ve got a recipe for, dare I say, the ideal Caribbean holiday.

The next morning we feast on French toast, bacon, and fresh tropical fruit, one of three meals per day that—along with alcoholic drinks and on-the-water toys like stand-up paddleboards, kayaks, and a 12-foot, outboard-engine-powered dinghy—is included in a crewed Moorings charter. So with pineapple mimosas poured, we await the captain’s daily briefing. He tells us that we can snorkel at a nearby archipelago called the Indians (widely regarded as one of the top dive sites in the British Virgin Islands); search for ballast stones, sea glass, and naturally occurring salt crystals on Salt Island; or explore the white-sand beaches of Cooper Island, a 480-acre islet that’s home to a small family-owned resort but little else. We raise our hands for all three and sail off into the BVI breeze.

After a full day of uninhibited exploration, even our dinner later that night is a surprise choice. While anchored off Cooper Island’s Manchioneel Bay, we’re met by a local fisherman who motors up next to our yacht and asks if we’d like some freshly caught lobster. It’s a request that my wife and I can hardly pass up, so we’re handed two clawless crustaceans, which Shannon expertly prepares in the galley, alongside garlic mashed potatoes and prosciutto-wrapped asparagus.


We didn’t see another soul at Sandy Spit, a one-acre cay surrounded by clear-blue water.

Photo by David LaHuta

Things go like this for the duration of our trip, but some choices, admittedly, come easier than others. “Are we gonna go back to Virgin Gorda, Daddy?” asks my eight-year-old son, Tyler. My family was last there in 2019, on a similar crewed charter that created memories galore, so we instruct the captain to sail northeast en route to the BVI’s third-largest island, so named because Columbus thought it resembled an overweight woman lying on her side when he discovered it in 1493.

Following a near mandatory amble through the Baths—a watery maze of school bus–size boulders formed by an ancient underwater volcano—we’re presented with our on-land lunch options: a hilltop barbecue joint called Hog Heaven where the panoramic view, we’re told, is as good as the smoked brisket, or fresh seafood and island-inspired tapas at the Sugar Mill, a beachfront restaurant at the recently reopened Rosewood Little Dix Bay. It’s one of our toughest decisions thus far, but the payoff comes as soon as we dig into plates of tuna belly tataki and seafood paella at a breezy table near the sand at Little Dix.

In fact, the resort is one of a trio that we visit that have either shined up or completely rebuilt their properties following the devastating impacts of Hurricane Irma in 2017. Reopened in December 2020, this grand dame of the Caribbean received a massive $200 million renovation—a Herculean effort to restore its rustic-luxe look considering that Little Dix was virtually blown away in the storm. Another was Saba Rock, a boutique luxury resort on a one-acre cay where captain Richard and Shannon took us for cocktails one evening. And the third was Oil Nut Bay, a 300-acre community on the North Sound of Virgin Gorda where its sprawling villas (including some that rent for $30,000 a night) looked spiffier than ever.

“So where to next?” asks captain Richard after stepping back onboard the yacht. At this point we realize that wherever he suggests will likely hit the jackpot, so we defer to his expertise and sail north, next to schools of wild dolphins and over galaxies of golden starfish. This day’s destination is Anegada, a flat atoll where we snorkel at a blissful patch of coral aptly named Flash of Beauty, eat blackened mahi-mahi tacos at the Anegada Beach Club, and drink rum punches at the Cow Wreck Beach Bar while the boys play on its seemingly endless beach.

It proves to be yet another adventure-filled day; of course, Richard has a few more anchorages in his arsenal that emphasize the territory’s current throwback vibe. He sails us west for snorkeling at a popular dive site called Diamond Reef, a place that’s typically teeming with shallow-water divers, but today, there’s not another swimmer in sight. Next, we anchor off Sandy Spit, an uninhabited one-acre cay that’s home to nothing but three spindly palm trees, piles of sun-drenched coral and my family of four. Then he plants us off White Bay on Jost Van Dyke, and we’re pleased to be one of only four boats in a cove that’s normally chock full of charters. We can’t believe our eyes, so after swimming to shore we make a beeline for nutmeg-topped Painkillers and ring toss at the Soggy Dollar Bar, a beloved BVI rum shack where we barely have to wait for our second (and third) round of cocktails.

With seven days behind us, our charter has officially reached a critical mass on the adventure scale, so the captain poses one last query for our journey’s ending: We can overnight at Jost or sail onward toward Tortola for dinner on the aft deck in a secluded bay called Smugglers Cove. Ever the sailor, my wife chooses the cruise, so the four of us ascend the stairs to the fly bridge, where we enjoy the wind in our hair, the sun on our faces, and a final champagne toast to a destination filled with glorious choices.

In the BVI, a crewed four-cabin Moorings catamaran starts at $2,500 per person, per week, including meals and alcohol; without a crew, rates start at $1,375 per person.

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