It's Always 'Five O'Clock Somewhere' at These Top 10 Key West Bars

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.



The battle over Hemingway's favorite watering hole ends here. Captain Tony's Saloon was the original location of Sloppy Joe's (and its previous incarnation as a speakeasy) where the famed author haunted a bar stool until 1938. When the landlord...  Read More

Duval Street


This funky Duval Street bar is a must-do on any Key West itinerary. Female impersonators take the stage at the cabaret, including the legendary Sushi, who has been making a name for herself on the island for more than 25 years. Expect singing,...  Read More

Duval Street
Aqua Nightclub
Photo courtesy of Aqua Nightclub


This all-welcome, gay night club has creative events every day of the week from afternoon to evening. Stop in for no-limit Texas Hold'em poker tournaments, Aqua's American Idol karaoke with proceeds that go to charity and dueling bartenders who...  Read More



The Little Room Jazz Club & Wine Bar is a refreshing change amidst the Duval Street Troprock scene. Find a new favorite glass of wine from the extensive listing, as you listen to live jazz, blues and even Cuban-fusion bands. A 70-inch...  Read More



With eight bars built in to this complex, you can easily party all night at Rick's Key West. The Duval Street institution offers late night karaoke (until 4:00 a.m.), the Durtbags cover band, and several DJs that turn up the bass into the wee...  Read More

Duval Street


Located on Duval just next to the Tropical Inn, Vinos on Duval it's a refreshing change of pace. The intimate environment invites conversation, and sharing a bottle and cheese plate is the way to go. They have an extensive selection of reds,...  Read More

Duval Street


Nestled between Key West Harbor and Mallory Square, Sunset Pier is all about location, location, location. Of course the live music,vivid decor, Caribbean fare and lip-smacking libations don't hurt either. Each night thousands of visitors flock...  Read More

Duval Street


Steps from the controlled chaos on Duval Street, The Porch is a craft beer lovers refuge tucked into the front of a 1839 Victorian mansion. They have 18 brews on tap and plenty more in bottles with selections changing with the seasons. Wine...  Read More



Filled with mix of local characters and visitors-in-the-know, "The Parrot," is not your typical dive bar. As the oldest watering hole in Key West, they've got nothing to prove, and their motto, "No Snivelling," illustrates their no-nonsense...  Read More



Stop by and visit with the friendly mixologists at the Rum Bar at the Speakeasy Inn (an actual former speakeasy from the Prohibition days). While the staff at the fraternity-style pubs on Duval Street toss together a Jack and Coke, these...  Read More


Meet Claudia Miller

Claudia Miller has been writing about South Florida for over 17 years--seven from Key Largo. A budding photographer, she can usually be found stalking a sunset. Despite being a tad...  More About Claudia