Travel Tip: Take Tradewind
Here’s why: Unmatched in the Caribbean for both comfort and convenience, the charter airline recently started offering regularly scheduled flights from San Juan, Puerto Rico, to the islands of Nevis, Anguilla and St. Barths. The VIP service on the eight-seater planes is worth every penny—because while the airline handles customs and immigration, you can enjoy another complimentary glass of Veuve Clicquot. From $345 one way; 800-376-7922; flytradewind.com.
Staying on Tortola
As the travel hub to and from the BVI, Tortola offers limited solace. However, Frenchmans Cay (on the island’s secluded southwest coast) is home to two standout villas: the five-bedroom Frenchman’s Lookout (from $750 a week) and its three-bedroom sister property, Frenchman’s Paradise (from $450 a week). Both are tranquil oases worth sticking around for. 888-546-5008; inspirato.com.
New Virgin Gorda Villa Alert
Valley Trunk, on Virgin Gorda’s southwestern tip, way east in the BVI, was formerly an exclusive playground for the billionaire Wildenstein family. Its enviable distinction as the only residence on Valley Trunk Bay’s beach means the clan’s compound—which debuts for rent this season and comes with their 68-foot yacht—is as private as it gets. Villa starts at $200,000 a week for up to 16 people; 284-495-5611; valleytrunk.com.
Rum Punch Rundown
Leave the artisanal cocktails to the pros at urban speakeasies: On the islands, the one drink you can’t go wrong with is the traditional blend of fruit juices with white and dark rum. Spots serving our favorites: Pavilion Bar (Old Rd., St. Mary’s; 866-502-2855; campbellgrayhotels.com) at Antigua’s Carlisle Bay; Scotchies (Falmouth Rd.; 876-953-8041) in Jamaica’s Montego Bay; Basil’s (St. Vincent; 784-488-8350; basilsbar.com) on Mustique; and Nevis’s Sunshine’s Beach Bar (Pinney’s Beach; 869-469-5817; sunshinesnevis.com), where the stingingly sweet concoction is aptly named the Killer Bee.
The Dominican République?
Oui. Embrace the French Caribbean lifestyle at the six-room Peninsula House (rooms, from $550; Las Terrenas; 809-962-7447; thepeninsulahouse.com) on the Samaná Peninsula, a European expats’ haven northwest of Punta Cana. It’s a two-hour drive from Santo Domingo’s airport, which means two things: The region isn’t overrun with tourists, and the resort’s helipad is an appealing arrival option.
Three More Islands
For anyone thinking “been there, done that,” three out-of-the-way retreats offer an extra measure of the unexpected. At Secret Bay (rooms, from $360; Tibay, Portsmouth; 767-445-4444; secretbay.dm), the six villas are a great base from which to explore the wild terrain of Dominica (a two-hour flight from San Juan). Named after the island it sits on, Petit St. Vincent Resort (rooms, from $1,100; 800-654-9326; petitstvincent.com) is about two hours from Mustique by boat; 22 stone guest cottages rest on its 115 acres. A five-minute sail from Grenada, Calivigny Island’s ($ from $30,000; 48-607/404-064; calivigny-island.com) Balinese residences rent to one group at a time, perfect for reenacting Gilligan’s Island—with 50 of your closest friends.
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