Going Where the Wind Takes You

In the opinion of many travelers, a “bareboat” vacation—in which you and your companions charter a sailboat for a week or so, load it with provisions, and head wherever the trade winds and your imagination take you—is the ultimate way to explore any island chain. And there’s no better place to launch your own sailing adventure than in the bareboat capital of the world: Tortola, the largest (19×4.8km/12×3 miles) and most populous of the British Virgin Islands.

In terms of convenience, safety, affordability, and sheer number of attractive places to drop anchor, the 60-plus islands and cays of B.V.I. are tailor-made for the do-it-yourself island hopper. The capital of the British Virgin Islands, Road Town, nestled on Tortola’s mountainous southern coast (the island’s beaches are all on the northern, Atlantic side), is home to dozens of charter companies with well-maintained catamarans and single-hulled boats to choose from. (Powerboats and full-sized yachts with crew are also available.) Sail out of the town’s well-protected natural harbor, and you’ll find yourself a couple of hours away from Norman, Peter, and Cooper islands, all awaiting with white-sand beaches, reefs perfect for snorkeling, sheltered coves for anchoring overnight, and waterfront bars and restaurants that cater to the seaborne set. The larger islands of Virgin Gorda, to the northeast, and Jost Van Dyke, off Tortola’s northern flank, are both less than a day’s sail away. Scattered about are scores of uninhabited islets that are yours for the claiming.

The key to any successful bareboat vacation is advance planning. Charter companies all ask you to submit a “sailing resume” proving you have enough experience to handle their boats. The official B.V.I. tourist site, www.bvitourism.com, has a long list of reputable charter companies with links to their websites. While prices vary, bareboat vacations tend to be remarkably affordable, typically costing about as much as a cruise. If you’re worried about rusty sailing skills, you can charter a boat with an extra sleeping space or two and pay for your own skipper and cook. In addition to knowing the best spots to drop anchor, the crews-for-hire in Tortola are also accustomed to blending in with new boat mates. For a little extra, you can even request a captain who’s a certified sailing instructor.

Sailors aren’t the only active travelers enjoying Tortola’s sparkling seas. Divers and snorkelers have much to explore here, most notably the wreck of the HMS Rhone, a British Royal Mail steam packet ship that sank here in an October storm in 1867. The wreck lies in depths from 6 to 24m (20–79 ft.) just south of Tortola near Salt Island. Reserve a dive with Blue Water Divers ( 284/494-2847; www.bluewaterdiversbvi.com) to the site of the Rhone and other gems of the deep.

For those who prefer to spend their time on solid ground, Tortola has its share of fine resorts and villas, all imbued with the relaxed, friendly, non–theme park atmosphere (no casinos here, thank you!) for which the B.V.I. are known. The beaches on Tortola are actually quite wonderful, from popular Cane Garden Bay, wrapped in soft green hills, to the secluded sands of Long Bay, where you can swim and snorkel in clear, gentle seas.

With half its income coming from tourism and the other half from the financial industry (the island is headquarters to many of the world’s offshore companies), and a currency based on U.S. dollars, Tortola is an enchanting blend of old world and new. And when you’re out in the archipelago, the wind filling your sails, it’s all yours to discover. —AF

www.bvitourism.com.

Tours: Moorings, Wickham’s Cay ( 888/952-8420 or 284/494-2331 in the B.V.I.; www.moorings.com).

Tortola: Beef Island International Airport, connected to Tortola by the Queen Elizabeth Bridge.

Regular ferries from St. Thomas, U.S.V.I. (45 min.).

$ Ole Works Inn, Cane Garden Bay ( 284/495-4837; www.quitorymer.com). $$$ The Sugar Mill, Apple Bay ( 800/462-8834 in the U.S., or 284/495-4355 in the B.V.I.; www.sugarmillhotel.com).