1. Best Island: Bermuda

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A subtropical archipelago of 181 volcanic islands, Bermuda won the bid to host the 2017 America’s Cup, thanks to near perfect North Atlantic sailing conditions. Beyond wind, the British Overseas Territory, just a two-hour flight from New York City, has 75 miles of pink-sand beaches interspersed with jagged limestone cliffs, many of which are perfect for deep-water soloing and hucking into the Atlantic from the top. Stay at Elbow Beach, a 50-acre hideaway with a private stretch of sand on the southern shore (from $455).