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The island: Virgin Gorda, British Virgin Islands
The goods: The BVIs are surrounded by seas and swept by breezes that make them perfect for sailing. And nowhere does it get more lively than in the waters of Virgin Gorda, whose North Sound is a favorite overnight anchorage for boats by the hundreds. Even landlubbers can get caught up in the atmosphere just by showing up at the Bitter End Yacht Club at happy hour.
Be sure to: Get afloat in a sailing yacht, most easily done by staying at the all-inclusive Bitter End. They have a fleet of more than 100 boats at the disposal of hotel guests, a learn-to-sail program, and even the option to spend nights sleeping aboard a 30-foot sailboat with room for four.
Best beach: The Baths is a tumble of house-size rocks where filtered sunlight illuminates pools of blue water and patches of white sand that are the perfect setting for falling in love—or running into somebody you know from Connecticut.
Perfect season: Any time from December to April except Spring Break, when it becomes apparent just how many families can afford to charter a yacht.
Call it home: Even the shoreside villas at Bitter End are close enough to the sailing action that you'll want to fall asleep to the lullaby of sea shanties.
Bitter End Yacht Club
Tel: 284 494 2746
Villas from $630