Ernest Hemingway, Truman Capote, Shel Silverstein, Tennessee Williams and the Mayor of Margaritaville himself, Jimmy Buffet, have all enjoyed a drink at Captain Tony’s Saloon in Key West, Florida, which makes it one of Florida’s most beloved landmarks. A must on any Key West Itinerary, Captain Tony’s Saloon is not just the state’s oldest bar, but it’s also a piece of living history.
Originally built in 1851 as an icehouse that doubled as a morgue, Captain Tony’s Saloon offers you the chance to have a cold beverage where legends have been drinking for decades. Sitting on Greene Street, immediately upon entering you’ll notice the that is is the epitome of a dive bar with its license plates on the walls, bras, business cards and dollar bills strewn from the ceiling. The bar stools have famous patron’s names on them, and there’s even a “hanging tree” where 19 pirates met their fate growing in the middle of the bar.
Not much has changed here since Hemingway was a regular and ordered his scotch and soda. At the turn of the century, it was used as a cigar factory, speakeasy and then used as a bootleg distributor of rum, but it wasn’t until 1933 that Sloppy Joe’s opened and became a favorite for Hemingway. Captain Tony’s pub grew throughout the 20th century and added a billiards room, cementing it as an iconic Florida beach bar named after the late captain Tony, a maritime icon that was once a fishing boat captain gunrunner, gambler and Mayor of Key West.
Considered one of the last pieces of old Key West, the bar is also where Jimmy Buffett got his start, as he was a regular performer in the 1970’s and was often paid in tequila. A perfect respite on a hot summer day, come here to cool off with a glass of their famous Pirate Punch. The staff here are known for offering a warm welcome and its atmosphere is unparalleled, where you can catch live music every night and mingle with a crowd of locals and tourists alike.
Before you leave, admire the large Jewfish above the sign outside that Captain Tony caught and preserved. It’s said that if you throw a quarter into the mouth of the fish you’ll have good luck until you leave the island.
Captain Tony’s Saloon:
Official Website
