Sloppy Joe's Bar is a live music venue in Duval Street, Key West.
Editorially verified August 21, 2026 by Lewis Vaughan, TableJourney editor. Source.
Tip: The operator dates the bar to 1933 and this corner to 1937; July's Hemingway Look-Alike Contest is the rowdiest week to visit.
Address: 201 Duval Street, Key West, FL 33040
Hog's Breath Saloon works an open-air corner near Mallory Square, the Key West room of a saloon brand founded in Florida in 1976, with all-day bands.
Tip: Live music runs from 13:00 to close most days; the raw bar side is quieter than the stage side if you want to talk.
Irish Kevin's has run singalong sets on lower Duval since July 1998, a Key West show bar pouring Irish beer with a kitchen that serves until 23:00.
Tip: Entertainers work the crowd hard, so sit back from the stage if you would rather not be part of the act.
The Rum Bar pours one of Key West's deepest rum lists on the Speakeasy Inn porch, an upper Duval house whose basement once hid Prohibition bottles.
Tip: Ask the bartender to build a three-pour flight by island; the porch rockers are the best seats on upper Duval.
Schooner Wharf Bar has held the old Singleton shrimp-factory site on Key West's bight since 1984, an open-air deck of roosters, rum and live music.
Tip: Breakfast starts at 08:00 Friday to Sunday and 08:30 Monday to Thursday; the bar calls itself a last little piece of old Key West.
Hog's Breath Saloon works an open-air corner near Mallory Square, the Key West room of a saloon brand founded in Florida in 1976, with all-day bands.
Tip: Live music runs from 13:00 to close most days; the raw bar side is quieter than the stage side if you want to talk.
Irish Kevin's has run singalong sets on lower Duval since July 1998, a Key West show bar pouring Irish beer with a kitchen that serves until 23:00.
Tip: Entertainers work the crowd hard, so sit back from the stage if you would rather not be part of the act.
Berlin's hides behind A&B Lobster House above Key West's harbour, a leather-chair speakeasy the operator dates as a local favourite since 1947.
Tip: You can order the full A&B menu at the bar, and the cigar terrace overlooks the marina; jazz nights run in season.
General Horseplay mixes proper cocktails and pours craft beer on Caroline Street in Key West, with a hidden back bar opening nightly at 19:00.
Tip: The back bar opens at 19:00 and feels like a second, smaller venue; sister rooms include Mary Ellen's and The Roost.
The Rum Bar pours one of Key West's deepest rum lists on the Speakeasy Inn porch, an upper Duval house whose basement once hid Prohibition bottles.
Tip: Ask the bartender to build a three-pour flight by island; the porch rockers are the best seats on upper Duval.
