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.
Chart Room Bar ★ 4.2
$$duval-streetDaily 17:00-00:00
The Chart Room hides inside the Pier House Resort at mile zero of Duval, the wood-panelled Key West bar once frequented by Jimmy Buffett and Mel Fisher.
Tip: The keywesttourist guide notes Buffett and treasure hunter Mel Fisher drank here; the room seats barely a dozen, so go at 17:00 sharp.
The Smallest Bar ★ 4.0
$$duval-streetDaily 11:00-23:00
The Smallest Bar squeezes a full Key West cocktail list into 72 square feet on lower Duval, claiming the title of the tiniest bar in the United States.
Tip: The operator claims 72 square feet and America's smallest-bar title; the Key Lime Pie shot is the thing to order at the ledge.
Tiki House ★ 4.1
$$duval-streetDaily 12:00-02:00
Tiki House shakes zombies and mai tais with fresh fruit on lower Duval in Key West, the island's dedicated tiki room from the Horseplay bar family.
Tip: Happy hour runs 12:00 to 15:00 before the street gets loud; the rum build quality beats the location's spring-break stereotype.