Capt. Tony's, Key West

This is the original site of Hemingway's Sloppy Joe so it is only fitting that this is the first bar my now husband, Joe, dragged me to in Key West. In its earliest incarnation (1851), Capt. Tony's Saloon was a morgue and icehouse, then Key West's first telegraph station. It was also a cigar factory and a bordello before it became the original Sloppy Joe's in the mid-1930s (when Hemingway was a regular). Later, a young Jimmy Buffett sang here (he wrote his song Last Mango in Paris about it).

It is your basic, dark dive bar where people have put up their business cards and some have left other memorabilia (i.e. license plates and bras). They serve lots of beer and great rumrunners. They do NOT serve food here. In addition to the patron decorations, there is a bust of Hemingway, and a single photo of the author of The Old Man and the Sea fishing with Tony Tarracino, a onetime mayor and former owner.

Dress Code: Last Mango in Paris lyrics by Jimmy Buffett:

"I went down to Captain Tony's
To get out of the heat
I heard a voice call out to me
Son come have a seat
I had to search my memories
As I looked into those eyes
Our lives change like the weather
But a legend never dies"

captain tony's saloon is located in a 1851 historic building on greene street. this bar was originally named russell's in 1933. ernest hemingway convinced the owner joe russell to rename the bar sloppy joe's because joe "ran such a sloppy place". in 1937 russell had a disagreement with his landlord and moved the bar to duval street. today this historic bar is called capt. tony's saloon. capt. tony's is a fun place to drink and soak up old keys atmosphere.

Dress Code: casual.

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Came here as part of a "pre-wedding" party - and it was FUN! Live band was playing at the front; we sat toward the back, by the tree growing through the bar's ceiling! I was told later that this was Key West's "hanging tree", and that 75 people were hung from it! On the ceiling were hundreds of license plates from around the country, hundreds of brassieres (most signed), and thousands of business cards. It made it fun to stare at the ceiling, and made for some hilarious "bachelor party" type photos...

We were headed to Captain Tony's after hearing stories about it in Hemmingway lore.
However, when we arrived, the place was quiet and practically deserted. The bras were all still hanging from the ceiling though.

Dress Code: Very, very casual

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We stopped at Capt Tony's between visits to Hogs Breath and Sloppy Joe's. Capt Tony's is more divey than either, but also kind of a happy medium between the touristyness of Hogs Breath and the raunchiness of Sloppy Joe's. Good place to stop in to listen to live music, play foosball, or watch sports, but not a good place to bring your kids. We had a few Red Stripes, because their brew selection was pretty limited.

This bar brags that from 1933 to 1937 it was not only the original location of Sloppy Joes, but it was also Hemingway's hangout while he lived here during the same time period. In fact, Earnest Hemingway liked this bar so much, when it was remodeled, he acquired one of the old urinals and installed it as a fountain at his home a few blocks away.

Came here as part of a "pre-wedding" party - and it was FUN! Live band was playing at the front; we sat toward the back, by the tree growing through the bar's ceiling! I was told later that this was Key West's "hanging tree", and that 75 people were hung from it! On the ceiling were hundreds of license plates from around the country, hundreds of brassieres (most signed), and thousands of business cards. It made it fun to stare at the ceiling, and made for some hilarious "bachelor party" type photos

Captain Tony's is a must see and is after all- the original site of Sloppy Joe's. This Old Town Key West Bar is an authentic place; Dark, dank, humid salted air with a stale beer smell. Built in 1852 Capt. Tony’s is the oldest bar in Key West. Hemingway spend many time here between 1933 and 1937. Today the walls are decorated with underwear and the ceiling with thousands of business cards of customers who have put on the ceiling through the years. Check out Hemingway's original bar stool and his "hanging tree" (it grows through the roof).

If your looking for a fancy bar, go somewhere else!

Dress Code: What dresscode..........we're on Key West!!

While similar in many ways, two nightlife extreme opposites are Capt. Tony's Saloon and The Green Parrot. Capt. Tony's is where that Jimmy Buffett guy went to get out of the heat, and it has a funky, almost cave-like, atmosphere where you will very likely hear some local Buffett wannabe playing guitar and singing. Unfortunately, this is one of those places the "tourists" just have to see, so the best time to go is in the afternoon while they are all shopping for T-shirts.

Dress Code: The Green Parrot, on the other hand, is strictly a "locals" type bar and what is known as a "Buffett-free Zone". No Jimmy on the jukebox here (and whatever you do, don't ask for Buffett). "The Parrot" does, however, provide some of the best "Blues" in the Keys. Both local and imported talent poor their hearts out onstage at "The Parrot" on a regular basis. Try to get Vicky, the bartender, to sing for you. She is incredible (at both singing and tending bar).