While Cuba has been off-limits to most American travelers since 1963, in recent years cruise ships have started calling again and flights from the United States have resumed. Most visitors today...

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Havana (La Habana), Cuba

While most Americans have never been there, the word Havana still evokes images of candy-colored vintage cars; smiling musicians; and cigar-smoking and rum-sipping locals. Dive beneath the surface and you’ll find much more: world-class sports matches, historic sites and even a Chinatown. And while Havana may not be a global culinary capital, you can find delicious dishes in casual restaurants run out of private homes or in upscale spots with city and water views. As for shopping, you’ll be able to purchase souvenirs from photo books about Cuba to a hand-blended perfume in a bottle that is a throwback to another era.

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Cienfuegos, Cuba

As a port on Cuba’s southern coast, Cienfuegos has played an important role in the country’s history since it was founded in 1819, and it remains an important commercial center—a transit point for coffee, sugarcane and tobacco. The birthplace of famous Cubans such as singer Benny Moré and baseball stars José Abreu and Yasiel Puig, the city looms large in Cuban consciousness. It also boasts numerous attractions that give a fuller, more complex view of Cuban culture and history. This fact was recognized by UNESCO in 2005, when the historic center was added onto its World Heritage List.

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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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