Lou Giunta
Captain Tony’s is a legendary bar in Key West. It is reportedly the oldest bar in Florida. I had the pleasure of meeting Captain Tony many years ago and wanted to make sure I had at least one beer there while I was in Key West.
This place is the ultimate Key West vibe. There is cold beer, friendly service and live music every day. And of course, the atmosphere is “way laid back”.
Among the decor you will find dollar bills and bras hanging from the ceiling everywhere. The bar stool seats contained the names of famous people who had sat there over the years. I sat in the same seat as John Candy. Some very famous peoples stools were hung from this ceiling. (See picture)
If you’re looking for a real, authentic Key West experience, stop in and have a cold beer. You won’t regret it.
… moreRoss Lewis
This is an iconic Key West bar, if nothing else stop in just for the history story around the bar. We just grabbed afternoon drinks. Nothing fancy going on here, nice cocktail menu served in plastic cups (I now have a nice collection from all over the island!) and cold beer. Everything you need and nothing you don’t kind of place.
… moreGeorge Blooming
Tons of history and I can see how it’s a cool vibe. Walls and decorations are outstanding as well, once again so much history here! I wish I could rate it more but if you going for a casual beer and hanging out great, other than that they don’t have many set drink options from their small menu that they just kinda splat in front of you when you ask. It also had some kind of smell to the place, which I don’t know if it was the place itself from the old money and old bras covered in dust hanging from the walls or happened to just be the air kicking around but overall sat down, looked and left.
… moreKath UEP
Old school Key West bar! Was my favorite over our 4 days. Read the history on it – very cool. Live music fun. Patrons are a true friendly vibe. Shoutout to the couple from Daytona, you were funny. Bartenders are cool…1 grumpy, one funny, one adorable…liked em all. Grumpy in a funny way not a jerk. Ladies, leave your bra on the hangin’ tree. Surcharge on cc so cash is king.
… moreValdemar
Great little bar with a fun, relaxed atmosphere. Live music every night, talented local bands, and a good mix of people. Drinks were solid, service friendly, and the place has that true Key West vibe. Nice spot to hang out, listen to music, and unwind after a long day on the road. Would definitely stop here again.
… moreScouser1965
An absolute classic Key West Bar with a nice cozy interior and a real laid back vibe.
Prices are reasonable considering the location and we enjoyed our drinks listening to live music and taking in the history of the bar.
… moreRichard Coradi
This is Key West at its best. Historic building combined with drinking. Dark and historic. The bartender was really nice. People try to flip a quarter facing backwards into the big fish’s mouth that is over the door outside. We were here on 10/17/25.
… moreJason Hatfield
Best stop in Key West hands down. The live music is always a hit and will get those feet tapping to the beat quickly. Great drinks. Great atmosphere. Don’t forget to sign a dollar (or more) bill and pin it to the ceiling or walls.
… moreLil Y
I stopped in to see the spooky stuff– the grave by the tree (20 people were lynched on this tree) and another grave in the pool room. Also I heard the bottles in the wall were once filled with holy water in order to ward away evil entities. Awesome place!
… moreWanda Walters
My visit to Capt Tony’s was everything I’d hoped for and more. Hearing the history of the establishment from the staff was absolutely amazing to learn. Highly recommend while in the Keys Capt Tony’s is a must see.
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