If you can make it during the first week of May, you can catch the annual Carnival festivities, known here as Batabano. Keep walking, if you must, on the renowned Mastic Trail, which cuts through a rad a nature preserve. It’s free, though it’s worth paying a small fee (meaning a gratuity) for a guide to give you a more thorough experience. Not really an ocean person? That’s cool-you can go to Hell, a surreal landscape of black limestone. Maybe feed a stingray while you’re there. For a smoke show beach, which we're going to assume is one of your higher priorities, head a few minutes south to Seven Mile Beach. Visit the Cayman Turtle Centre to swim with sea turtles (and learn about local marine life).
On a short trip, you’ll get the most out of your time on Grand Cayman, the largest. Why you’ll love it: The Caymans are three islands, each with a different vibe. Aim for March or April, the sweet spot when hotel rates drop but the rainy season hasn’t quite yet kicked in. A round trip will run probably $300 to $550.
From Chicago or New York, it’s still under four hours. Travel time: You’re in Miami? Great! A direct flight for you is just an hour and a half.
