Imagine a perfect tropical island. Does it include lush volcanic peaks rising dramatically above the sea? Or maybe a palm-fringed beach with crystal clear water? Do you see, instead, a harbor dotted with yachts and lined with inviting restaurants and boutiques? Whatever your ideal island escape looks like, you are likely to find it in the Caribbean. The warm waters of the sea are host to some 7,000 different islands belonging to 28 nations. It is a varied lot in terms of topography—and culturally, too, with Americans, Dutch, English, French and Spanish, among others, having left their marks on this sun-kissed corner of the world. Now it’s your turn to explore it.
Half Moon Cay, Bahamas
Georgetown, Cayman Islands
Between the celebrity chefs who’ve set up shop on Grand Cayman and the 135 or so resident nationalities that season the island’s giant melting pot, this is one of the best places to eat in the Caribbean. In George Town, the Cayman Islands' capital, you’ll find such an array of culinary offerings, you’ll fear for the future of the buttons on your waistband. And that’s where the island’s other chief pleasures come in: Try to counter the effects of the extraordinary food by walking (whether along the fabled Seven Mile Beach, around historic sites or through lush gardens), swimming, snorkeling and diving the gorgeous waters.
Key West, Florida, US
One of the first things you’ll notice about Key West, after the colorful gingerbread wooden houses and the amazing sunsets, is the constant crowing of roosters. Hundreds of the birds—along with their quieter-clucking mates—roam the streets, and are nearly as synonymous with Key West as its six-toed cats, the famous furry residents of Ernest Hemingway’s mansion in the Old Town district. They’re all part of the quirky charm of the United States' southernmost point, whose compact 11 square kilometers (4.2 square miles) pack in everything from gorgeous historic architecture and spectacular fishing and sailing to a lively party scene along Duval Street.