Bermuda
More Carolina coast than Caribbean, really, the pink-sanded British overseas territory will play host to the Americas Cup in 2017 and is in a sweet spot for second homes—John Lennon and David Bowie (R.I.P.) both owned here; Mark Twain once famously described it as better than heaven. With Marcus Samuelsson’s new restaurant at the Fairmont’s Hamilton Princess & Beach Club, the food is getting there, too. 