With more bars per capita than anywhere else in the United States, Key West has a smorgasbord of watering holes. The island’s “It’s 5 o'clock somewhere mantra” means daytime drinking is perfectly acceptable, and finding the best happy hour is a sport. Key West’s rich rum-soaked history is filled with pirates, rum runners and famous writers.
The bar now known as Captain Tony’s has been slinging drinks since the days of Prohibition, and as the former home of Sloppy Joe's, it was Hemingway’s favorite spot for knocking back scotch and soda. Green Parrot, the oldest dive bar in Key West, has a solid rep as the best live music in town.
Along Duval Street, Old Town’s main drag, it’s easy to stumble into bars that cater to the beer and burgers crowd. Get the most bang for your buck at Rick’s, which combines multiple bars and clubs into one complex.
Hidden treasures like The Porch, a craft beer lovers refuge, are worth seeking out. While the Rum Bar at the front of the aptly named Speakeasy Inn features rums from around the world. If you’re in the mood for something mellow, Vino’s is a wine-lover's paradise, and the Little Room Jazz Club has soothing live music nightly. For a view of the famed sunset, plant yourself on a colorful stool at Sunset Pier slightly removed from the masses on Mallory Square. Old Town is pedestrian friendly, and these bars were made for hopping.