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...

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Half Moon Cay, Bahamas

If you've ever dreamed of having your own private island, Half Moon Cay in the Bahamas offers the opportunity to fulfill that fantasy. Also known as Little San Salvador Island, Half Moon Cay is located southeast of Nassau. In 1996, Holland America Line purchased the island and set aside most of it as a wildlife sanctuary. At 10 square kilometers (four square miles), the island is small enough that you can see it all in a day, yet large enough to offer an array of activities: horseback riding, snorkeling with stingrays, a range of water sports and, of course, simply lounging on the beach.

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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.

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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.

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Cozumel, Mexico

Cozumel, an island in the Caribbean off of Mexico's Yucatán Peninsula, draws scuba divers, snorkelers and sun seekers. The island also offers all other manner of on- and around-the-water attractions, many of which are unique, such as underwater sculpture gardens, a submarine excursion and a sailboat-racing experience. For visitors who are intrigued by Mexico's Maya culture, there are several archaeological sites near Cozumel, including the UNESCO-inscribed Chichén Itzá and, on Cozumel itself, San Gervasio, where women once made offerings to the goddess of fertility. When you're done sightseeing, there's shopping for traditional Mexican crafts, jewelry and leather goods, including custom-made sandals, and excellent food.

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Oranjestad, Aruba

Located off the coast of Venezuela, the windswept Dutch island of Aruba is otherworldly. The beaches are spectacularly pristine, the waters are romantically restless, the lunar-like interior is filled with cacti, and the trees are—famously—bent in the wind. The consistent trade winds that shape the trees are part of the destination’s allure: They keep the humidity, rain and even hurricanes at bay. The main port and capital city, Oranjestad, is a maze of Dutch-colonial architecture painted in a palette of Caribbean pastels. Farther afield, lighthouses, gold mine ruins and natural wonders reflect the rugged appeal of Aruba.

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