Key West, Florida Keys, Florida
The final stop on the Eastern Seaboard's 2,369-mile Route 1, Key West really is the be-all and end-all. Geographically, Key West sits at the southernmost point within the continental U.S. and is closer to Havana than it is to Miami. In spite of its tropical climate (Key West boasts an annual average temperature of 77 degrees) and its low-lying land, Key West is hit by hurricanes less than other coastal regions.
While Key West is enthralling in and of itself, be sure to make it out to sea when in the area. Just a few miles off the coast is the third-largest coral-reef system in the world, the Great Florida Reef. Snorkeling, diving, and deep-sea fishing are popular area adventures. Man-made reefs offer wreck diving just a few miles offshore, too.
Key West was once home to Ernest Hemingway and Tennessee Williams, among other celebrities of yesteryear. These days, its most famous residents come in a more natural variety: iguanas, feral chickens and roosters, and a clutter of cats—the latter of the excessive-toe variety, nestled in Hemingway's former home.