My family and I have just boarded our 50-foot chartered catamaran, and the wind is whipping through our hair as we enter Sir Francis Drake Channel, a deep blustery strait that connects much of the British Virgin Islands. Our captain, a scruffy, bearded Texan named Tyrone LaRue, points out Dead Chest Island, an uninhabited knob where the pirate Blackbeard marooned his crew with nothing but a saber and a bottle of rum. The legend inspired Robert Louis Stevenson's song “Dead Man's Chest,” which appeared in Treasure Island. According to local lore, only a handful of the crew made it. We sing the sea chantey, or at least the “yo-ho-ho and a bottle of rum” part, and imagine what these waters were like then.
Geographically speaking, not much has changed. Sailors know that the over 50 isles in this British Overseas Territory east of Puerto Rico still provide calm, protected coves, and that the trade winds, which consistently move from east to west, make this archipelago one of the finest boating destinations in the world. What is less common knowledge is that chartering a yacht here, as well as in many vacation spots around the globe, can cost less than a luxury resort.
This is a relatively new phenomenon. When The Moorings, the company my family worked with, began operations in the British Virgin Islands in 1969, it had six 35-foot Pearson yachts, tight-quartered, two-cabin monohulls that required extensive sailing know-how and deep pockets. Back then, The Moorings was the sole charter company in the region. These days, its diversified fleet is more than 400 strong in more than 20 destinations—a success story that has encouraged tech-savvy newcomers like GetMyBoat and Yachtico to get in on the charter game and try to appeal to Gen X and millennial travelers. Like The Moorings, they offer crewed yachts where a captain and first mate do the work, as well as “bareboat” charters, where guests with certified licenses can take the helm, significantly lowering costs. With thousands of ultra-modern vessels available to book, some of which sleep 12 comfortably, charter companies are courting younger generations who crave not only the freedom granted by a sailing vacation but also the value it can provide.
Charter yachts are also great options for families with young kids, like mine. The yacht we picked up in Road Town, Tortola, the largest and most populated of the BVI, was more like a fully kitted-out floating home than a traditional sailboat. In addition to the high-tech extras (solar-powered water makers and push-button winches), it had modern bathrooms, air-conditioning, spacious seating, and luxe amenities like a bow trampoline with plush beanbag chairs, a teak swimming platform, and a 12-foot dinghy. And, of course, we could take it wherever we wished. Unlike cruise ships, which have set itineraries and designated ports, charter boats let you choose your own adventure. This flexibility is particularly apparent in the BVI, since unlike other popular sailing archipelagos (such as French Polynesia), all of the islands are within sight, which means you don't have full days of sailing to reach your next stop. You basically wake up, decide where you want to go next, and arrive within an hour or so of active sailing.
Back on the water, Tyrone is busy tacking and jibbing through the white-capped sea when my young sons, Jackson and Tyler, ask to sit at the helm. Once they're installed behind the wheel, Tyrone resumes his geography lesson. We learn that the Virgin Islands were named by Christopher Columbus in honor of Saint Ursula, a fourth-century Catholic saint, and the alleged 11,000 virgins who were martyred alongside her. Tyrone also tells us where we're headed: the tiny 1,779-acre Peter Island.
From Tortola it takes about 45 minutes to reach Peter Island, and we anchor in a calm bay where there's not much more than the setting sun and a handful of other boats. About an hour later, savory smells waft through the galley and out to the aft deck, where my wife, Joy, and I are relaxing with cold glasses of Minuty rosé. Tyrone is grilling pork tenderloin; Jess, his first mate and wife, is busy whipping up asparagus tips with a brandy cream sauce and a sweet-potato mash.
The following morning, we awake to poached eggs on avocado toast. It's time for the captain's daily briefing. “The plan is to circumnavigate the B.V.I.,” says Tyrone, holding a colorful map for us all to see. He quizzes the boys on where we've been and tells us that our next stop will be Cooper Island. After Jackson feeds a school of blue runners from the swim platform and we've begun sipping our first round of pineapple mimosas, we're off. Forty minutes later we drop anchor in a quiet cove called Manchioneel Bay and swim the 30 yards to shore. We beach comb for sea whips and intact urchin tests—the creatures' spiny exoskeletons—then hike up a steep, brush-lined slope to Cooper's highest point.
From atop the breezy hill we have a bird's-eye view of Virgin Gorda—a voluptuous volcanic island so named because Columbus thought its profile looked like an overweight woman lying on her side. The next morning we're there, and our excitement builds as we anchor near its most impressive natural attraction, a national park called the Baths, where massive granite boulders form grottoes you can wade into. It's a magical morning that gets even better when Tyrone arranges for a taxi driver to escort us to Hog Heaven, a mountaintop barbecue spot where the fall-off-the-bone ribs are almost as epic as the panoramic view.
The rest of the week follows a similar cadence of exploration and relaxation. We visit Anegada, a pancake-flat atoll where feral donkeys and goats roam free, flocks of flamingos splash in muddy marshlands, and visitors explore dusty roads in Mokes, classic British open-air vehicles. Eventually, we end up at Cow Wreck Beach Bar, on the island's northern tip, where we mix our own rum cocktails and tally our tab on a notepad. The joint, perched on a white sand beach with license plates and faded flags nailed to its wooden rafters, is as close to a Kenny Chesney song as you can get. Other days we follow Tyrone on under- and above-water adventures. One afternoon we snorkel through schools of blue-striped grunt near Monkey Point, off the southern tip of Guana Island; on another we explore Norman Island's water-level caves, where we swim past blooms of moon jellyfish. On the 163-acre isle of Little Jost Van Dyke, we trail Tyrone down a narrow goat path to the Bubbly Pool, where crashing waves fill a small rock pool with frothy seawater, creating a sort of natural jacuzzi. And one afternoon we make the near-mandatory swim to the Soggy Dollar Bar on Jost Van Dyke, wet cash in hand, and order painkillers (a cousin of the piña colada) while the boys play ring toss in the sand.
Our last day is one for the family annals. We have some of the best snorkeling of the trip near the unfortunately dubbed Indians, a group of rocky outcroppings shaped like tipis, where we snorkel over kaleidoscopic coral and through schools of reef fish so thick we have to part them with our hands. Then Tyrone takes us to Pirates Bight, a peaceful cove that's home to a retrofitted tanker-cum-bar called the Willy T, where locals and visitors jump into the water from its second-floor deck, despite clearly posted signs advising to the contrary. Before we know it, Tyler, our youngest, jumps, and the rest of us follow. That night we have a fantastic last meal back on the boat. The thought of leaving is hanging heavy in the air as Joy and I put the kids to sleep in their cabin and then head to the top deck for one final nightcap under the stars. The breeze is warm, the sky is black, and we watch as Orion's Belt slowly rises across the Milky Way.
This article appeared in the September/October 2021 issue of Condé Nast Traveler. Subscribe to the magazine here.
