The Roost is a bar in Old Town, Key West.
Editorially verified August 21, 2026 by Lewis Vaughan, TableJourney editor. Source.
Food program: 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.
Address: 508 Fleming St, Key West, FL 33040
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.
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.
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.
Signature drink: Pirate's Punch under the hanging tree
Food: No kitchen; drinks only
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.
Schooner Wharf Bar has held the old Singleton shrimp-factory site on Key West's bight since 1984, an open-air deck of roosters, rum and live music.
Signature drink: Pina colada on the harbour walk
Food: Seafood, breakfast from 08:00 and bar plates
Order: A pina colada with fish and chips at the dock rail
Tip: Breakfast starts at 08:00 Friday to Sunday and 08:30 Monday to Thursday; the bar calls itself a last little piece of old Key West.
