Berlin's Cocktail Bar & Lounge ★ 4.4
$$$historic-seaportDaily 17:00-23:00
Berlin's hides behind A&B Lobster House above Key West's harbour, a leather-chair speakeasy the operator dates as a local favourite since 1947.
Tip: You can order the full A&B menu at the bar, and the cigar terrace overlooks the marina; jazz nights run in season.
General Horseplay ★ 4.3
$$historic-seaportMon-Fri 15:00-02:00; Sat-Sun 12:00-02:00
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 ★ 4.6
$$duval-streetDaily 11:00-23:00
The Rum Bar pours one of Key West's deepest rum lists on the Speakeasy Inn porch, an upper Duval house whose basement once hid Prohibition bottles.
Tip: Ask the bartender to build a three-pour flight by island; the porch rockers are the best seats on upper Duval.
801 Bourbon Bar ★ 4.5
$$duval-streetDaily 12:00-04:00
801 Bourbon Bar anchors upper Duval as Key West's best-known drag room, with the 801 Girls performing nightly above a bar that pours until 04:00.
Tip: The downstairs bar is the walk-in room and the cabaret upstairs is the show; go late, because the bar runs to 04:00 every night.
Aqua Bar & Nightclub ★ 4.4
$$duval-streetMon-Thu 14:00-00:00; Fri-Sat 14:00-02:00; Sun 14:00-00:00
Aqua runs Key West's drag programme across a Duval Street complex of bars that includes the Birdcage Cabaret, the Back Bar and 22&Co under one roof.
Tip: The complex is several rooms rather than one bar, so check which room the night's show is in before you queue at the front door.
Captain Tony's Saloon ★ 4.3
$duval-streetMon-Sat 10:00-02:00; Sun 10:30-01:00
Captain Tony's Saloon drinks inside an 1851 icehouse on Greene Street, the Key West bar that claims Hemingway's patronage and a tree through the roof.
Tip: The operator says the building was an icehouse and morgue and that Hemingway drank here; both bars on this block claim him, so enjoy the argument.