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Best for Sailing
More than 30 tiny isles (most uninhabited) stretch out like an unfurled sail for 45 miles in the southeastern Caribbean. Each has its own distinct flavor: Mustique is where the rich, famous, and infamous hide out in multimillion-dollar villas; the quiet fishing (and once whaling) island of Bequia has its salty dogs; Canouan is the home of the 1,200-acre Raffles Resort; and off-the-map Mayreau has only one road and just got electricity in 2003.
If you really want to get to know the Grenadines, chartering a sailboat is key. Captain your own yacht or hire a professional skipper through the Moorings (moorings.com; four-berth yachts from $5,180 per week). If you plan to island-hop without a boat, know that ferries and flights between islands have restricted schedules, and almost everything routes through St. Vincent—so even though most islands are less than an hour apart by boat and just 10 minutes by air, you could spend half a day in transit.
Worth the Splurge
Late British stage and costume designer Oliver Messel transformed a former 18th-century cotton warehouse and sugar mill into the 17-room Cotton House (Mustique; 888/452-8380; cottonhouse.net; doubles from $615). The two-bedroom Cotton Hill Residence, with its own pool, sprawling gazebo, and personal butler, offers the utmost in privacy. Don’t miss the Tuesday-night cocktail party in the Great Room, when villa owners and their guests—such as Tommy Hilfiger, Mick Jagger, and Bryan Adams—descend from the hills for community social hour.
Overlooking the crystalline waters off Bequia’s southeast coast, Friendship Bay Beach Resort (Bequia; 784/458-3222; friendshipbay.vc; doubles from $240) proves that "barefoot luxury" is more than an expression. This contemporary colonial hideaway—the only beachfront hotel on Bequia—meshes rich mahogany, travertine marble, private plunge pools, and pebbled floors in 25 rooms and suites to create a comfortable oasis, where even the Swedish owner never dons shoes.
Though each island has breathtaking swaths of powdery white sand (Pasture and Macaroni Beach on Mustique, Princess Margaret Beach on Bequia), the real treasure is the kaleidoscopic blue-green waters of the Tobago Cays, a five-island wildlife reserve where parts of Pirates of the Caribbean were filmed. Day-trippers swim with sea turtles and stingrays and snorkel among acres of coral reef tiled with starfish. If that sounds too strenuous, drop anchor in a secluded cove with a pink-coral beach. The Friendship Rose (784/495-0886; friendshiprose.com; $100), a 96-foot schooner, sails to the islets twice a week from Bequia. Captain Yanni (yannissail.com; $65) has catamarans that depart daily from Union Island.
The owners of Firefly Mustique unveil a six-suite sister property, Firefly Bequia (Spring Valley; 784/488-8414; doubles from $575), this month on Bequia.
At Basil’s Bar (Mustique; 784/488-8350; dinner for two $85), the food is simple: burgers, grilled lobster, shrimp Creole. But the dockside open-air restaurant is a veritable institution, with rock stars, supermodels, and fishermen mingling late into the night.
Where to Shop
For the ultimate in island chic, stop by the Pink House (Britannia Bay, Mustique; 784/488-8521), Lotty Bunbury’s new boutique. In addition to her caftans and pareus—staples for any Mustique wardrobe—the pastel gingerbread cottage also carries designs by other part-time residents, including Elle McPherson and Elizabeth Hurley.
You don’t have to be a hotel guest at Raffles Canouan Island (Canouan; 784/458-8044; raffles-canouanisland.com; doubles from $575) to use the RafflesAmrita Spa. Purchase a resort day pass ($110) and book a sea salt–and-eucalyptus scrub in one of the new glass-bottomed, thatched-roof palapas, which are accessible by dinghy from the spa’s private dock.
—Jennifer V. Cole