Captain Tony’s Saloon is a historic bar at 428 Greene Street in Key West, known for live music, low-key drinks and walls covered with signed dollar bills. The building dates to 1851 and has served as an icehouse, a morgue and the original Sloppy Joe’s Bar. Ernest Hemingway spent time here before the bar moved across the street; Captain Tony Tarracino took over in 1958. Order a beer or Pirate’s Punch, take in the memorabilia and listen to the music. It can get crowded, so quieter hours are better if you want a table.
A building with several past lives
The Greene Street building dates to 1851, when it served as an icehouse and a morgue. It later had other uses, including a wireless telegraph station, a cigar factory, a bordello and a speakeasy.
From 1933 to 1937, it was the original Sloppy Joe’s Bar. Ernest Hemingway spent time there before the business moved across the street. In 1958, local boat captain Tony Tarracino bought the bar and gave it the name it carries today.
The tree and the walls
A tree grows through the bar’s interior. It is associated with the site’s history as a place of hangings, and is often called the hanging tree. The bar’s walls and ceiling are covered with signed dollar bills and other bits of memorabilia, giving the room much of its character.
You can add a signed dollar bill to the collection. Outside, there is also a fish sculpture that people try to hit with a tossed quarter.
Drinks and live music
The bar serves beer and Pirate’s Punch, which can come in a souvenir cup. Live music is part of the regular scene, and the bar stays open late. The atmosphere is casual, with a large central bar and a cozy interior. If you want a seat at a table, choose an off-peak time; the room can fill up.
Perguntas frequentes
Was Captain Tony’s Saloon the original Sloppy Joe’s?
Yes. The bar was the original Sloppy Joe’s from 1933 to 1937, before it moved across the street.
What is the history of the building?
It dates to 1851 and was used as an icehouse and morgue. Later, it housed a telegraph station, cigar factory, bordello, speakeasy and bar.
What should I order at Captain Tony’s Saloon?
Beer and Pirate’s Punch are supported options. Pirate’s Punch may be served in a souvenir cup.
When is a good time to visit?
Go during off-peak hours if you want an easier chance of finding a table.
