Cocktail barOpen-air harbour bar$$historic-seaportDaily 08:00-02:00
Schooner Wharf Bar has held the old Singleton shrimp-factory site on Key West's bight since 1984, an open-air deck of roosters, rum and live music.
Signature drink: Pina colada on the harbour walk
Food: Seafood, breakfast from 08:00 and bar plates
Order: A pina colada with fish and chips at the dock rail
Tip: Breakfast starts at 08:00 Friday to Sunday and 08:30 Monday to Thursday; the bar calls itself a last little piece of old Key West.
Cocktail barOpen-air saloon$$duval-streetDaily 10:00-02:00
Hog's Breath Saloon works an open-air corner near Mallory Square, the Key West room of a saloon brand founded in Florida in 1976, with all-day bands.
Signature drink: Hog Snort
Food: Raw bar, fish tacos and hog legs
Order: Fish tacos and a Hog Snort during the afternoon set
Tip: Live music runs from 13:00 to close most days; the raw bar side is quieter than the stage side if you want to talk.
Cocktail barRum bar$$duval-streetDaily 11:00-23:00
The Rum Bar pours one of Key West's deepest rum lists on the Speakeasy Inn porch, an upper Duval house whose basement once hid Prohibition bottles.
Signature drink: Rum flight from a list in the hundreds
Food: Drinks only; restaurants within a block
Tip: Ask the bartender to build a three-pour flight by island; the porch rockers are the best seats on upper Duval.
Cocktail barCocktail bar$$historic-seaportMon-Fri 15:00-02:00; Sat-Sun 12:00-02:00
General Horseplay mixes proper cocktails and pours craft beer on Caroline Street in Key West, with a hidden back bar opening nightly at 19:00.
Signature drink: House cocktails and tasty beers
Food: Bar snacks and small plates
Tip: The back bar opens at 19:00 and feels like a second, smaller venue; sister rooms include Mary Ellen's and The Roost.
Cocktail barNeighbourhood bar with kitchen$$old-townDaily 11:30-02:00
Mary Ellen's serves grilled cheese down an Appelrouth Lane alley until 02:00, the late Key West kitchen that beats a pizza slice after Duval Street.
Signature drink: Boozy slushies with a grilled cheese
Food: Nine grilled cheeses plus Bad Boy Burrito
Order: A grilled cheese from the nine varieties, with the dipping sauces
Tip: Appelrouth Lane is easy to walk past; the kitchen serves late, which makes it the grown-up alternative to pizza slices.
Cocktail barTiki bar$$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.
Signature drink: Zombie with fresh pineapple
Food: Drinks only
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.