Of all the bars in Key West, Captain Tony’s Saloon contains more colorful history than any other. The oldest licensed bar operating in the State of Florida and the original Sloppy Joe’s, the stories are plentiful.

Tony’s is another one of those Key West tourist bars these days, just a few steps off of the Duval Street drag on Greene Street. You don’t see very many locals or regulars any longer, but the Captain still stops by to greet customers, sell some T-shirts and pose for photos with the tourists. And he can still tell some fascinating stories of the old Key West, including his friendship with Jimmy Buffet who wrote about Tony in his recording “Last Mango In Paris”.

One of the very first impressions you get when you walk into Captain Tony’s is the darkness and dingy looking walls, a testament to the age and history of the building. I personally find it really fun to just walk around (with a cold beer in my hand) and check out the memorabilia on the walls and hanging from the ceiling, including more business cards than I have ever seen in one place and a collection of bras that I’m sure continues to grow.

For a few years there was a pending trademark dispute between Sloppy Joe’s Bar and Captain Tony’s Saloon. After some lengthy litigation, the courts ruled in Tony’s favor and allowed him to continue advertising as “The Original Sloppy Joe’s Bar”. It makes sense as 428 Greene Street was the original location for Sloppy Joe’s and was the bar that Hemingway visited most afternoons for a scotch & soda.

Housed in a building constructed in 1851 with a rich history, Captain Tony’s is a must see for Key West tourists. Originally a morgue that sidelined as an ice house, once a telegraph office that spread the news of the sinking of the battleship Maine in 1898, a cigar factory, a speakeasy, a bordello and gambling hall, Sloppy Joe’s Bar, a gay club and finally Captain Tony’s Saloon opened in 1958. Oh… let’s not forget the “Hanging Tree” that now grows inside Tony’s Saloon and out through the roof.


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Considering that Captain Tony was born in 1916, he has now crossed into the Nonagenarian decade of his adventurous life. I expect Tony never thought he would last this long after a brutal beating in 1948 where he was left to die lying in a New Jersey dump. He did survive and made his way to Miami, gambling away all but $18 and hitch hiking to Key West on a milk truck.

Captain Tony stories abound in Key West. His first ten years in Key West were occupied as a charter boat captain, who also did some gun running for Cuban mercenaries during the Bay of Pigs. Tony had some spare time to produce thirteen children from three wives. And back some years ago the Key West citizens, fed up with local politicians, voted Captain Tony mayor.

Key West just wouldn’t be the same without Captain Tony’s Saloon, Make it a point to stop by.

3 Responses to “Captain Tony’s Saloon”

  1. I visited Capt Tonys in January of 2007. Ended up spending the whole day there. Great place, even went back in the eveving and met Tony himself. I placed my school ID card on the ceiling. Looking forward to returning this fall.

  2. Great Place!!! I placed one of my business card on the ceiling a couple of years ago. About six months later I got a call from a friend. He was sitting in Tony’s, looked up and saw the logo on my card, and called. Pretty neat! He was pretty drunk and having a good time.

  3. i lived in key west in 1974 and 1975. i knew capt tony he was a great man.i loved hanging out at capt tonys. it was a great plsce then and i still stop in when i go to key west. love the place and love capt tony