Before Sloppy Joe’s moved to Duval, this was Hemingway’s actual bar, and it’s been collecting history ever since. Built in 1852 as an icehouse and city morgue, 428 Greene Street is now Florida’s oldest bar, soaked in legends both literary and macabre. Barstools painted with the names of Hemingway, Truman Capote, Jimmy Buffett, and JFK. A live hanging tree growing up through the roof. Two gravestones under the pool table. Dollar bills and bras covering the ceiling. Jimmy Buffett got his Keys start playing here for tips and tequila: he immortalized it in “Last Mango in Paris.” Order a Pirate Punch, throw a quarter in the grouper’s mouth for luck, and let the stories wash over you. This is not a bar. It’s a time machine.
Part of the full rundown on the best beach bars in the Florida Keys.
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