Jess Swanson, Senior Editor

Key West is the southernmost city in the continental United States, connected to the rest of the country by a series of scenic bridges across an archipelago of barrier islands. Only 90 miles from Cuba, the island romanticizes this distance with a slower, quirkier way of life. Once home to Ernest Hemingway, Tennessee Williams and even President Harry Truman, Key West proudly embraces its eccentricity to this day. The town offers literary festivals, Victorian mansions, breathtaking sunsets and, of course, the boozy shenanigans on Duval Street.