5 late-night dives in Key West our editors have drunk at, sorted by score. All Key West nightlife.
Captain Tony's Saloon ★ 4.3
duval-street · 428 Greene St, Key West, FL 33040
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-street · 1 Duval Street, Key West, FL 33040
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-street · 124 Duval St, Key West, FL 33040
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-street · 203 Duval Street, Key West, FL 33040
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-town · 420 Appelrouth Lane, Key West, FL 33040
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.