Captain Tony's Saloon
Florida's oldest bar was a morgue, then an ice house, then a telegraph station. Hemingway drank here. A hanging tree grows through the roof.
The building at 428 Greene Street in Key West has been many things: a morgue in the 1800s, an ice house, a telegraph station, and — from 1933 to 1937 — Sloppy Joe's Bar, where Ernest Hemingway was a regular. When Sloppy Joe's moved to its current location on Duval Street, the original space became Captain Tony's Saloon. It has been operating continuously ever since, making it the oldest bar in Florida.
A live tree grows through the roof of the bar. It was used as a hanging tree in the 19th century. The remains of 75 bodies — discovered during a renovation — are buried beneath the floor. The bar is built around all of this.
The walls are covered in business cards, bras, and signed photographs accumulated over decades. Jimmy Buffett played here before he was famous. The bar stools are occupied at noon on a Tuesday. The whole place smells like history and spilled beer, which is exactly right. Captain Tony Tarracino — the bar's namesake — was a rumrunner, gambler, and eventual mayor of Key West. His portrait hangs above the bar.
Located at 428 Greene St, Key West. Open daily from 10 AM to 2 AM. No cover. Cash preferred. The hanging tree is visible from the bar — look up. The gravestones embedded in the floor near the entrance are real. Go on a weekday afternoon before the cruise ship crowds arrive.