From the days of the rumrunners and speakeasies, Key West has earned a solid reputation as a party town. In fact, the tiny island has more bars per capita than any other place in the country. Every night the revelry starts at the carnival-style Mallory Square Sunset Celebration filled with fire-eaters, tightrope-walkers and trained cats. From there, many people head to the well-known bars located on Duval Street, the main drag in Old Town. Irish Kevin’s is right in the thick of it with bawdy musicians energizing the crowd. For something more hip, The Porch features craft beers and wine. If you want to head off the beaten path, Kokomo Joe's Off Duval Bar Crawl walking tour is the perfect fit.
For a dose of culture, you can catch a show at the Waterfront Playhouse or hit up the Little Room Jazz Club for live music. Virgilio’s is a also classy joint with swanky people dancing and downing some of the best martinis in town. There’s an active LGBT community on the island, and Aqua Nightclub is a straight-friendly spot for funky events and high-energy dancing. The Cabaret at La Te Da hosts drag queen divas who perform with no lip-synching. Late night, head to the ultimate dive bar, the Green Parrot, to mingle with the locals and listen to some of the best live blues, funk and rock around. Just remember, a lot of crazy stories begin with, “...and then we went to ‘The Parrot.’”