Key West, Florida
Closer to Cuba than to Miami, the southernmost city in the continental United States can feel like a country all its own. Home to free spirits, scuba divers and six-toed cats, Key West is defined by its quirky charm. People go barefoot, chickens roam the streets and eclectic culture rules. Architecture lovers will appreciate classic Caribbean villas, unique Keys conch houses and Victorian and Queen Anne gingerbread homes. Shopping opportunities range from many music and book shops to trendy designer boutiques.