Best Island:Bermuda

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).