Cayman Islands

The air is casual, but the scenery is totally luxe — a hard-to-find combination in the Caribbean.

Take a catamaran to chart the islands' teal-blue waters, letting the reliable trade winds show you around. There are hundreds of dive and snorkeling sites, too, including Sting Ray City and Turtle Beach -- here, try to spend as much time on the water as you do on land.

The north side of Grand Cayman Island — and back on solid ground — is where you'll find the locals. Rum Point is a never-disappointing good time, but if you roll a bit slower, Cayman Brac, a much smaller, even quieter island than its grander counterpart, might be your speed. It's a tiny slice of Nirvana popping out of the ocean.