General Horseplay is a bar in Historic Seaport, Key West.
Editorially verified August 21, 2026 by Lewis Vaughan, TableJourney editor. Source.
Food program: 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.
Address: 423 Caroline Street, Key West, FL 33040
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.
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.
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.
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.
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.
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.
