Cocktail barNovelty bar$$duval-streetDaily 11:00-23:00
The Smallest Bar squeezes a full Key West cocktail list into 72 square feet on lower Duval, claiming the title of the tiniest bar in the United States.
Signature drink: Key Lime Pie shot off the shotski
Food: Drinks only
Tip: The operator claims 72 square feet and America's smallest-bar title; the Key Lime Pie shot is the thing to order at the ledge.
Cocktail barSpeakeasy$$$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.
Signature drink: Slow-sipped classics with a cigar terrace
Food: A&B Lobster House menu served in the lounge
Tip: You can order the full A&B menu at the bar, and the cigar terrace overlooks the marina; jazz nights run in season.
Cocktail barHotel dive bar$$duval-streetDaily 17:00-00:00
The Chart Room hides inside the Pier House Resort at mile zero of Duval, the wood-panelled Key West bar once frequented by Jimmy Buffett and Mel Fisher.
Signature drink: A cold beer amid the room's stacked memorabilia
Food: Complimentary bar snacks
Tip: The keywesttourist guide notes Buffett and treasure hunter Mel Fisher drank here; the room seats barely a dozen, so go at 17:00 sharp.
Cocktail barCocktail bar and liquor store$$old-townDaily 12:00-23:00
The Roost pairs serious old fashioneds with caviar service half a block off Duval in Key West, doubling as the neighbourhood's corner liquor store.
Signature drink: Wednesday old fashioneds
Food: Caviar service, smoked salmon and deviled eggs
Tip: Happy hour runs 12:00 to 18:00 and the caviar-and-cosmopolitan order is the move; bottles to go from the shop shelves.
Cocktail barIrish pub and show bar$$duval-streetDaily 11:00-03:30
Irish Kevin's has run singalong sets on lower Duval since July 1998, a Key West show bar pouring Irish beer with a kitchen that serves until 23:00.
Signature drink: Irish beers with singalong sets
Food: Burgers, wings and pulled pork sliders until 23:00
Tip: Entertainers work the crowd hard, so sit back from the stage if you would rather not be part of the act.
Cocktail barDollar-bill bar$$duval-streetMon-Thu 10:00-02:00; Fri-Sat 10:00-04:00; Sun 10:00-02:00
Willie T's papers its Duval Street porch in signed dollar bills and pours mojitos over live music from 11:00 to 01:30, with a full Key West seafood menu.
Signature drink: Fresh-mint mojito
Food: Full seafood and burger menu, late-night service
Order: A fresh-mint mojito and whatever fish is on the board
Tip: Add your own signed dollar to the tens of thousands on the walls; the kitchen serves lunch through late night.