Berlin's Cocktail Bar & Lounge is a bar in Historic Seaport, Key West.
Editorially verified August 21, 2026 by Lewis Vaughan, TableJourney editor. Source.
Food program: 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.
Address: 700 Front 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.
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.
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.
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.
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.
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.
Signature drink: Cold draft with free popcorn
Food: Free popcorn only; bring your own food
Tip: There is no kitchen, only free popcorn, and outside food is welcome; soundchecks around 17:30 are a show in themselves.
Sloppy Joe's opened with Prohibition's end in 1933 and has held Duval and Greene since 1937, a National Register Key West saloon with all-day live music.
Signature drink: Sloppy Rita
Food: Sloppy Joe sandwiches, wings and bar snacks
Tip: The operator dates the bar to 1933 and this corner to 1937; July's Hemingway Look-Alike Contest is the rowdiest week to visit.
