George Town, Grand Cayman
Great for: Dining, shopping, wreck dives, swimming with stingrays
If you’ve only got six hours: Take a short boat ride to Stingray City, a sandbar where you’ll literally be surrounded by rays. Afterwards, enjoy a drink at Rum Point.
For those who want to experience the Caribbean but aren’t quite ready to dive head-first into the island culture, Grand Cayman is an absolute paradise. The food here is unmatched, with restaurants from the likes of Eric Ripert, plus an annual culinary cookout that draws A-list food celebs from the world over.
Grand Cayman is also home to the Kittiwake, one of the coolest wrecks in the Western Hemisphere. And the shopping at Camana Bay is, like the restaurants, as good as you’ll find anywhere in the States.