Down in Key West, its Sloppy Joe’s on Duval Street that draws the raucous crowds. But we prefer the more locals flavour of Captain Tony’s Saloon, right around the corner on Greene Street. After all, its not every bar that has Victorian period gravestones embedded on the floor by the pool table, or the old town hanging tree right in the middle of the bar, or was once a morgue. This peculiar history shouldn’t come as a surprise – for we’re in the oldest bar in Florida. It also happened to be Hemingway’s favourite spot.


This charming bar, painted a vibrant yellow, was actually the original Sloppy Joes, back in the 1930s. When the rent was raised by a dollar a week, owner Josie Russell moved the famous bar to Duvall Street, and the old place was bought by Captain Tony Tarracino. But the building itself has a much longer and macabre history.

The first thing you’ll notice walking in, is the large, still living tree right in the middle of the bar, its top poking out of a hole in the roof. This was once Key West’s gallows! Its set in what was once a courtyard – the bar was later built around it. Its thought that at least 75 people met their fates here, mostly hung for piracy. 


If that’s not odd enough, wander around Captain Tony’s and look down at the floor – dotted around are genuine, 19th century gravestones. During refurbishing work in the 1980s, the floor boards were taken up to reveal the final resting places of between 15-18 people. Among them, a gravestone for a young woman named Elvira Drew was discovered. She’s the unfortunate resting next to the pool table. 


Elvira was married, in her mid-teens, to an abusive, alcoholic man in his fifties. Elvira left the world in 1822 at the tender age of 19, hanged on winter solstice nearly two hundred years ago for killing her husband in self-defense. 

But perhaps our favourite thing about the Captain Tony’s Saloon, is the gravestone placed underneath the old hanging tree. Sitting up at the bar, an elderly lady in her 80s told us this story : 


“It belongs to Reba I. Sawyer, who lived used to live here……when she died, her husband found scandalous letters between his wife and another man. The letters detailed their trysts, and how they would arrange to meet at Captain Tony’s Saloon. The widowed husband dragged his cheating partner’s tombstone from the cemetery into the bar, placed it under the tree, and supposedly said “this is where she wanted to be, so this is where she will stay”.

For those who like a little morbidity with their evening cocktail, there’s only one place to head in Key West – Captain Tony’s Saloon.

What You’re Having:  The same as Ernest Hemingway; a daiquiri made the proper way, without a blender.  428, Greene Street, Key West, Florida, 33040. www.capttonysaloon.com


  1. A very cool history! I’ve always loved a good “old” bar and I’m always on the hunt for a new interesting one. This will surely be on my list.

    • Its one of our favourites! Most people head to Sloppy Joes when down in Key West, without knowing that the original one
      is just around the corner! Glad you enjoyed it. We post a new bar every Friday, and most of them are old!

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