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
$$duval-streetDaily 12:00-02:00
Tiki House shakes zombies and mai tais with fresh fruit on lower Duval in Key West, the island's dedicated tiki room from the Horseplay bar family.
Tip: Happy hour runs 12:00 to 15:00 before the street gets loud; the rum build quality beats the location's spring-break stereotype.
Mary Ellen's Bar & Kitchen ★ 4.2
$$old-townDaily 11:30-02:00
Mary Ellen's serves grilled cheese down an Appelrouth Lane alley until 02:00, the late Key West kitchen that beats a pizza slice after Duval Street.
Tip: Appelrouth Lane is easy to walk past; the kitchen serves late, which makes it the grown-up alternative to pizza slices.
The Green Parrot ★ 4.8
$old-townSun-Thu 10:00-02:00; Fri-Sat 10:00-04:00
The Green Parrot has poured at Whitehead and Southard since 1890 by its own count, Key West's open-shuttered dive with free popcorn and nightly bands.
Tip: There is no kitchen, only free popcorn, and outside food is welcome; soundchecks around 17:30 are a show in themselves.