Considered the sailing capital of the Eastern Caribbean, hundreds of yachts from around the world converge on the island during the last two weeks of April for its Classic Yacht Regatta and Sailing Week to race, play, and generally show-off. Insider tip: on race days, the restaurant atop Shirley Heights near English Harbour serves a fantastic Caribbean Buffet lunch with killer views.
peeterv
Bahamas
If you’ve not a yacht of your own, and can’t tie knots, consider joining one of Intrepid Travel’s seven-night, fully crewed catamaran sailboat tours. Departures are from Marsh Harbour, the commercial heart of The Abacos, and take in no fewer than seven remote cays along the way.
Flavio Vallenari
St. Vincent and the Grenadines
What is so lovely here is that you’re never far from sight of land, even if it’s just a tiny, uninhabited speck in dazzling, turquoise waters. A ten-day idyll might begin on St. Vincent and take in Mustique, Canouan, Mayreau, the Tobago Cays, Union Island, and Bequia. Each anchorage is more shockingly beautiful than the next.