Havana (La Habana), Cuba

While most Americans have never been there thanks to the U.S. government’s embargo of Cuba which started in 1962, the very word Havana still evokes a set of specific images—candy-colored vintage cars puttering along picturesque streets; smiling musicians playing familiar tropical tunes whose rhythms are so infectious that nearly everyone is seduced into dancing; cigar-smoking and rum-sipping locals against a palm-fringed background. There’s a reason these have become the stereotypical visual symbols of Cuba’s capital city, but dive beneath the surface and you’ll find so much more: world-class sports matches, centuries-old historic sites and even a Chinatown in midst of a cultural revival. And while Havana may not be a global culinary capital (for the moment, at least), you can find plenty of delicious dishes served in friendly casual restaurants run out of private homes or in more-upscale spots with city and water views. As for shopping, you’ll definitely be able to purchase unique souvenirs to take home, from photo books about Cuban culture sold at the island’s only English-language bookstore to a hand-blended perfume or cologne packaged in a bottle that looks like a throwback to another era.