Sailing the Caribbean by Catamaran

With a sailboat and a sense of adventure, go rediscover the British Virgin Islands—you're guaranteed an entirely different experience than you've ever had there before.

What a thrill it is to discover one thing while in pursuit of another. You may think you know the British Virgin Islands: the predictably beautiful beaches, breezy trade winds and swarms of sunburned tourists. Then one day, needing a quick break, you try out a whirl in a 47-foot catamaran—and voilà! Magic happens. During my eight-day trip to the Caribbean, that’s just the 180 I experienced. It changed my view of the region permanently.

Day 1: Getting to know you

Our get-acquainted dinner is in an open-air restaurant in Nanny Cay, Tortola, where 41 flotilla guests size each other up. A flotilla is like a tour group on boats, and most of us start out as strangers. There is a lot of energy and laughter. On hand are organizers Peter and Carol King, of King Yacht Charters. My husband, Douglas, and I will be with them on the lead boat.

Day 2: Crisis averted

The docks are a hive of industriousness. We lug our stuff to our catamarans (known affectionately as “cats”) and move in. Mountains of food are delivered. We fill the freezer with enough fish, chicken and beef to feed an army. Mark, our professional flotilla skipper, arrives. A handsome South African in his 50s, he has a buttery accent of such elegance that I wonder what he’s doing with this group, instead of broadcasting news for the BBC. One by one, the four boats shove off from the docks, with a professional skipper on each for the day to teach everyone the ropes of sailing. Because we’re in the lead boat, we’ll keep Mark for the duration. We hoist the sails, catch the breeze and rocket toward Cooper Island. By noon, we’re swimming in liquid turquoise.

That evening, we join the gang onshore to order ribs and icy beer at the Cooper Island beach restaurant. Someone screams, “A cat’s drifting toward the beach!” Mark leaps from his chair to a dinghy and tears out to intercept the drifting boat, returning calm as a cucumber to resume his dinner. “They didn’t tie the line properly to the mooring,” he says. “No harm done.”

Day 3: The perfect day

We set sail for the Baths at Virgin Gorda. Huge, rounded boulders, each the size of a Prius, balance artfully atop one another along the beach. We tie the boats to moorings and watch as all the seat cushions fly out of the cockpit of one of them in a burst of wind. Karla—a former competitive swimmer and our fellow flotilla member—dives in to retrieve them. (She has numerous other calls to arms during the week as boat hooks and dinghies go floating off.)

We linger at the baths, swimming and exploring like children in the natural pools, then sail behind the reef at Scrub Island. The glassy anchorage is surrounded by verdant hills. There’s a cool breeze. We rest, read and swim. That evening, a skiff from Donovan’s Reef restaurant picks us up for dinner: blue cheese–and-apple salad, seared scallops on a nest of cappelini with tomato concasee, and grilled yellow-fin tuna. Sailing is so often about the food you get to eat afterward.

Day 4: Ramping up

Under a clear sky and helped along by a strong breeze, we soar with the wind at our backs from Marina Cay to North Sound and the Bitter End Yacht Club. While we swim, nap and dream of our next feeding, Mark takes the dinghy from crew to crew, reviewing sailing instructions and charts for the next day. This will be the longest sail of the week—twentysomething miles across the boisterous Anegada passage, then dodging reefs into the anchorage. Mark thinks everyone’s ready for it.

Day 5: Excitement in the air

We take off for the Anegada sail, reaching speeds of 11, 12 and finally 13 knots as our cat hits its stride, whizzing past monohulls slogging at a poky 6 knots. Exhilarated and triumphant, we snake through the reefs and into the shallow anchorage. After hiking around the beautiful sand spit island, we have dinner onshore. Someone plays the guitar, and we sing along; Mark acts out a hilarious yarn about Prince Charles’s wedding night. It’s an evening of laughter, everyone telling stories about the day’s sailing adventures.

Day 6: What would mom and dad say?

We set sail toward White Bay, a spectacular crescent beach of white powdery sand that’s home of the Soggy Dollar bar, the birthplace of a drink called the Painkiller. Reaching this bar is our noble quest for the day. I join the folks on another boat for a rowdy breakfast of rum-soaked French toast and mimosas. These mates are irreverent, loud and impressed that Peter and Carol—whom they call Mom and Dad out of earshot—had the prescience to put together this particular group, to somehow know that despite the difference in their lifestyles, ages and tastes, they’re all of the same varsity party-animal caliber. (When I ask Mom later why she chose this particular group, she shrugs and says, “They were all engineers.”)

Music blares loudly all morning from an iPod as we whoop and sail at top speeds toward White Bay. After mooring, we dive into the clear water and float around the boat, awed by the pale-green color of the water. Several in our group swim ashore. The rest of us grab shirts and take dinghies to the beach to wiggle our toes in the sand and rock in hammocks under the palm trees. Several Painkillers later, we motor around the corner and anchor in Great Harbor. Just as we turn up the tunes and pop open a few cold ones, Mark swings over in the dinghy to take me back to the civilized ritual aboard our catamaran—where, he says, the kettle is on for afternoon tea. I leave, reluctantly.

This is the first time the flotilla will anchor for the night, rather than tie up to permanent mooring. Here, there are no handy mooring balls awaiting us, so one by one, the cats come into the anchorage and circle around looking for a good spot, like dogs chasing their tails. One cat is anchor-challenged. The crew finds a clear spot, drops the anchor and chain and puts the boat in reverse, hoping the anchor will hook in the sand below, but the boat drags. They pull up the chain and anchor, circle around again, drop again, then drag again, over and over. They can’t get the anchor to dig in. It’s painful to watch. Everyone in the harbor is mesmerized, grateful it’s not happening to them. Finally, the anchor hooks! Everyone cheers—even people we don’t know. I see the wisdom in Mom and Dad’s itinerary: Almost all of our evening stops have moorings.

Day 7: I came, I saw, I jumped

After a tropical-fruit breakfast, we sail to the Indians, a towering outcrop of rocks named after the Amerind Indians who used to inhabit the islands. We snorkel through kaleidoscopic coral beds along great rock walls covered in swaying coral.

Our final stop is the Bight at Norman Island, where the happening joint is Willie T’s, a barge restaurant. There’s a standing challenge at Willie T’s: Anyone who jumps naked off the third-floor deck platform at night, then presents herself downstairs at the bar, will be given an “I Came, I Saw, I Jumped at Willie T’s” T-shirt. Two from our group strip down and jump into the abyss holding hands in front of 100 or so stunned patrons. The jump won’t make them legends, but this will: They climb back aboard, stroll through the parting crowd to the bar and order shots while awaiting their T-shirts. Buck naked.

Day 8: Homeward bound

As we sail toward Nanny Cay, the days when we were banging against docks like bumper cars are long gone. Now the crews are well-oiled machines, tacking like champs. We’ve gone from disparate strangers—doctors, executives, business owners, teachers—to a warm group of sailors who have shared adventures, who know each other’s funny bones and foibles. Back at the dock, we hug good-bye. After a week of laughter and the pure beauty of sailing, we’re going home energized, with new skills, new friends and a fresh perspective on the sparkling Caribbean that can only be revealed from the deck of a boat.

BERNADETTE BERNON writes for Forbes Life, Islands, Boat U.S. Magazine and Cruising World, and she is the coauthor of the bestselling book Maiden Voyage (Simon & Schuster, 1989).