Captain Tony’s Saloon

Dive bar at it’s best, 22 ounce beer $ 5 keep the cup, refill for $ 4. Live music daily, has it own Key West charm

Best place ever! Always go there first when I get here. Feel at home! Great price. Music is great just enjoy yourself

Eclectic saloon with good music and inexpensive drinks. Friendly service. Nice place to dance. Points of interests; tree growing in middle of saloon, tombstone, and gravesite of lady buried in addition with bottles oh «holy water» in foundation! Fun place.

If you haven’t read Darlene D.‘s review of Captain Tony’s yet … just go read it because I couldn’t have said it any better than she did.
Steeped in rich history and tradition, the bar is worth the visit to say you’ve been. I’ve been and I can say, it kind of terrified me. Not in the scary terrified way, but the «God knows what noxious particles I’m breathing in by being in this grimy, cluttered, dusty, gloomy space» way.
The sheer number of dollar bills is only rivaled by the sheer number of brassieres… big, little, lacy, satin… many covered in years of dust and moth eaten now…
The coolest part is the old tree growing up in the center … and if you walk up to it, know you are literally walking on someone’s grave (again, refer to Darlene D.‘s review).
I ordered a draft beer just so I could get the cool souvenir cup (generous 20 oz pour). It didn’t taste funky so I can only hope that the draft lines are cleaner than the rest of the joint!
Definitely go to say you’ve been. If nothing else, it’s a pretty cool place to drop by and look around!

Nice and dive-​y, basically everything you would expect. The pirate’s punch is a bit pricey, ice-​y, and weak. It is, best I can tell, a tourist trap. Stick with beer.

My favorite bar in Key West. Good music, great bartenders and a friendly crowd, both local and visitors, makes this a great place to either take a break during the sightseeing day or somewhere to just sit and relax.
Everyone coming to Key West should plan on stopping in for at least one beer.

This is an authentic pirate bar. I chose to leave a dollar bill rather than my bra! Generous drinks and live music make this Key West bar a must see.

I love dive bars, this place is it. I ate the last mango in Paris.. had a 3^rd world girl in Buzios with a pistol in each hand… nuff said

The person who sang tonight probably started at 4 pm was completely insulting to customers. I asked for a request of a Mick Jagger song, said it was not relevant and told me to fuck myself

You visit because it IS.
Recommended.
We visited this place with locals commending it to us. You visit because it IS. The «décor» inside is unique: $ 1 bills, license plates, and autographed bras hang from the rafters. Don’t believe us? Check out our photo’s below.

Loved this one of a kind bar, first off you walk in and all you see is literally $ 1 bills stuck anywhere there is an empty space & to top that off an endless array of bras hanging above, loved it! The people, well I need say nothing its key west & the people are great & you can’t pick a better spot to just people watch.
Now speaking of the history is another story, if you plan on going you must google them to see how they began! Let me just tell you they began as a mortuary some hundred years ago, can you imagine. It truly doesn’t get better than that, good prices & great people watching spot with music & a dance floor, you can’t miss out on this one.

It is a bar in the purest sense. Hemingway drank here as did Buffett so I HAD to go. Had a night tasty and cold cocktail and listened to the music. Just a bar and tables, nothing fancy at all. It was a cool place to be after our day of exploring Key West.

Stopped by for a quick drink with family and enjoyed it. Of course when you enter you are overwhelmed with the bills and bras on the ceiling and walls. Really neat place to visit. It’s very open, a little dark inside, yet the workers are warm and friendly. The acoustic music was great on Sunday and the drinks were really good. The house Amber beer was delicious as well as the house punch. It’s definitely an older crowd, at least daytime. I’m not sure how this place is when it’s busy at night.

This bar is awesome! This bar reminds me of what bars in Key West are supposed to be like. I believe Jimmy Buffet got his start here. Great music and fun atmosphere. Don’t forget to leave your bra or your name on a dollar bill to leave a part of yourself after you’re gone.

If anything, Captain Tony’s is rich in history and most likely the matriarch of drinking establishments in old town. There is a tree on the inside (many Key West bars have trees growing through them), where they used to hang people back in the day, and don’t forget to pay a visit to the unofficial gravesite of Elvira who perished during a hurricane, which many people seem to overlook and walk right over in the pool room passageway.
The bar hasn’t changed a lick in 20 years, at least that I have noticed, except it is more run down. With the onslaught accumulation of business cards and paraphernalia over the years, the bar is dark and gloomy. The talent is mediocre at best, which is why I think most people have one and out. It’s boring.
If you haven’t been to Key West or visited this bar, I do recommend you stop here for a quick pop to see what it is all about. Take a moment to view the pictures of Captain Tony, an old salty dog with a witty sense of humor. He always liked to crack a dirty joke and ask for kisses from the ladies, as well as talk of tales long passed with his good friend Ernest Hemingway. A sweet soul who has recently passed a few years back. We love you Captain Tony!
Check out these intriguing historical facts including the mysterious haunting of the lady in blue. I just found this site, some pretty cool stuff to read about before you go…

This place just is off the charts fun. Sloppy Joe’s has the tourists coming in for a beer or two to say they were there. This place has the drinkers. The CHARACTERS. People are not there for just one. The musician when I was there sounded like he knew two guitar chords and should not be singing in his shower, if he takes showers. He was so bad he added to the charm of the place!!! Great time here!!!

When I was a kid first coming to the Keys with my family, I remember my Dad introducing me to an old guy that he said that I «had» to meet. I brushed it off as just another one of my Dad or Grandfather’s friends who fled for the Keys when it got to cold up North. It wasn’t until my 20’s that I found out that man was Captain Tony.
One of Captain Tony’s legacies in Key West is his saloon, on the site of the original Sloppy’s, one of the best dive bars around.
It has all of the traditional dive bar features that you’ve come to love in your lifetime of drinking your way through American History. Bras, dollar bills, and yellowed business cards that may have outlived their original owners litter the ceiling and walls. If you’re looking for some West End martini, go somewhere else, though I wouldn’t be quite sure how you ended up in Key West to begin with.
Come here for the light breeze, a few plastic cupped beers, and paying tribute to the bruised livers that came before you and sat in your very chair. It’s a must see and a must drink when in Key West.

4 Stars for the historical significance of this bar. The original Sloppy Joes. Captain Tony was quite a character in his time. Songs have been written about him and some the crazy stories about his are incredible. At one point he was mayor of Key West. I had the privilege of meeting and talking to Tony.
The bar is just your basic dive with god drinks and fun people. Look at all of the business cards and money stapled to the ceiling.

I’ll spare the history lesson of this place being the original Sloppy Joe’s and Hemingway’s old hangout… you’ll learn quick that Hemingway drank everywhere.
What I will tell you is that it’s a dive bar at it’s core. They have very few choices at all. 2 beers on tap and a few in cans. Can beer = dive bar. The 2 draft choices are Bud Light and Capt. Tony’s Amber. The décor is a bunch of crappy table and chairs, a game room, a small stage, gift shop and a big ass tree growing right up through the middle of the place and out the roof. That’s pretty cool. A ton of bras hanging from the ceiling, of course I wasn’t there to witness any freeing of the tatas.
You have to come to say you did and it’s probably cooler when they have live music other than that just living off the history.

Ein Muss für jeden Key West Besucher!

Really liked this place!
Bar tenders a lot of fun.
You have to have the tonys rum drink special though! Its very good and very cheap for what you get!
Interesting décor too… cash bills al over and bras on the ceiling.
Visited twice here within a week.
One of my fav bars for a drink though.