Key West

As the southernmost tip of the U.S. and the end of the chain of islands within the Florida Keys, Key West is known for its laid-back culture, azure seas, water sports, vibrant nightlife and rich history. Spanning only about 7.4 square miles, which includes 1.5 of those square miles as water, the city of Key West is very compact. Key West's Historic District is on the western side of the island in what is known as Old Town, where the original settlement of the island was located. Old Town is centered by lively Duval Street, which is the main drag in town with many hotels, inns, shops, restaurants and bars. Most of the island's best attractions are all located within close proximity of Duval Street and the island is easy to navigate due to its small size.

Key West is certainly the central hot spot for nightlife and entertainment, but great bars and restaurants can be found throughout the Keys. From rustic watering holes to live music venues, Key West has something for everyone, including a raucous pub crawl known as the Duval Crawl, sampling the street's finest in bars. Beyond the cocktails and nightlife, Key West also has many notable cultural attractions including the Tennessee Williams Fine Arts Center and the ever-popular Ernest Hemingway House. The author called Key West home for a number of years and is said to have written and worked on many of his most acclaimed books while living there. Getting out in the water is another favorite for most visitors and deep-sea fishing is especially popular in this region.