I stopped by Captain Tony's Saloon and it was such a fun, classic Key West experience. The vibe is exactly what you'd want, laid-back, a little quirky, and full of character. There was live music playing, pool tables, and even some video games, so there's plenty to keep you and the family entertained while you hang out. Kids are allowed in, but they aren't allowed to sit at the bar. It definitely feels like one of those places where you can lose track of time in the best way. They also have a merch area with hoodies, stickers, and other souvenirs if you want to take a little piece of the experience home. And knowing it's one of the oldest bars in the Keys just adds to the charm and history of the place. The service was quick, you walk up to the bar and order then find a place to sit. Super chill and laid back. One fun thing you have to try is tossing a quarter into the fish's mouth outside... test your luck and see if you can land it! Can't forget the drinks! The rum punch is to die for... super refreshing and perfect for the Key West heat. Overall, such a fun stop if you're in town. Definitely worth checking out! Fun fact: - it used to be a morgue and ice house back in the day. it also used to be the original home of Sloppy Joes, before they moved to Duvall St. read more

Captain Tony's Saloon - Oldest bar in Florida - Dive Bars Near Me - Key West, Florida

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We were with friends from CO who were visiting Key West for the first time. After walking around Mallory Square and down Duval Street, we decided to have a drink at Captain Tony's before going out to a different restaurant for dinner. Of course it is an attraction because it is supposedly the original Sloppy Joes where Ernest Hemingway hung out. It is dark inside with low ceilings. People have hung paper currency all over and you will also see lots of bras hanging from the ceiling. There is live music and lots of people watching. We enjoyed our drinks and the fun atmosphere. read more

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We had our second visit to Captain Tony's and this visit was even better than the first. We sat at the central bar and enjoyed a beer and people watching. We did a double take when we spied local celebrity, Lenny Chesney. Seriously, after a beer or two, across a crowded bar, and if you squint your eyes -- we were fooled at first! haha! He was so sweet and came over to talk to us and do a photo op. We loved his origin story and ability to carry out a long game prank. :) I also chose to leave a contribution to the decor and honored my beloved with an inscribed dollar. The bartender handed me a stapler and we placed it above my seat at the bar. Then, here's where the story becomes magical and spiritual -- I sat back down and happened to look across the bar and saw an older sailor seated with his wife, enjoying a cold drink. He was wearing a USS America CV-66 hat, which is the same aircraft carrier my husband served on during his military career. This is what we call a "godwink" moment and I'll take it. They were unbelievably kind to humor a stranger with a little conversation and I'll always have fond memories of this place for multiple reasons. The beer was cold and delicious. Bar stools are comfortable. Venue is easily accessible. Bartenders are top notch. read more

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Stopped by here twice during a recent trip to the keys. Once while bar hopping and once during a ghost tour. The place is larger than you'd expect and had live music when we went. We split their drink special (pirates punch) which came in a bucket. It was okay. They had dollar bill and bras hanging from the ceiling all over, which was pretty wild. I'm glad we went back during the ghost tour because we learned more about the place! There's a real skeleton behind the bar and a grave near the pool tables! There is a huge tree right next to the bar too that is real and used to be the towns hanging tree! I really enjoy spooky facts about the town so it made this bar just a little cooler in my mind! read more

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Looking for a place to leave your mark, maybe a dollar on the wall or a bra in the rafters? This is the place. Very loud, the band is great and you can feel to Music. Small bat so It takes a season to get there and get your drink once you arrive. Limited seating and air flow... very stuffy unless you're close to the door. Don't forget to feed the fish a coin! read more

Captain Tony's Saloon - Dive Bars Near Me - Key West, Florida

My favorite bar in Key West. You can find me here when I am in town. The beer is always cold and the music is always good. The bartenders are friendly. read more

Captain Tony's Saloon - Dive Bars Near Me - Key West, Florida

Only go here if you're looking for a dive bar with weak drinks. I was here early in the day from a cruise ship. They don't take Amex, but luckily my Apple pay. I was lucky they didn't have to put me to work. The bartender was friendly enough. The place is worth a walkthrough just for the pics. They had an entire area that was bras. That must have been from the drunk, late night crowd. read more

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Actually, we weren't there for very long. The music was OK. It felt kind of dirty to me so I didn't enjoy hanging out. I don't wanna feel like I'm gonna catch something lol But go in and enjoy for a few minutes if you like it stay don't take my opinion. I just felt like I needed to wash my hands! read more

Captain Tony's Saloon - Dive Bars Near Me - Key West, Florida

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Very cool place- we have actually just stopped for a drink. It's a unique in that the entire place is wallpapered in dollar bills I think this is a place that actually had a wall of bras hanging too. I just can't be sure- they all started to meld together. I wish I'd taken pictures. It was pretty dark though, and I didn't think it would show up. Definitely a place you need to stop in. read more

Historical and famous bar in the keys but not my preferred scene. We stopped in here on two occasions, the first was when we where bar hopping trying drinks from every bar we could. We split thier pirates punch or whatever the special drink was. It comes with a bucket, but we both didnt love it. The second time we came here was as part of our ghost tour where we learned all the lore of this place and there is a lot. A few key interesting parts is that they have a real human skeleton behind the bar. The bar is built around a famous hanging tree where they use to hang criminals back in the day and although the tree has since died they have the origional tree preserved in lacquer. Their are also said to be multiple Graves in the bar, one tomb stone on the tree and another on the floor near the pool tables. There are even more stories to this place but to say the least, some say it is haunted. read more

This was the first stop of our bar-hopping with the guys while ashore. I only had a punch drink and it was really good. Perfect amount to sweet (meaning, not too sweet) and I enjoyed the vibe and everything. read more

An average Key West dive bar. Loud, live music. Seems rather dark inside. The usually drinks. Service was okay. read more

Captain Tony's Saloon - Dive Bars Near Me - Key West, Florida

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Came back here with my group on my 49th Bday night and was serenaded by the band and the whole bar with " Happy Birthday" It was very cool!

When you are in Captain Tony's, you have the real feel of old Key West! Beverages are icy cold, service is terrific, and the one man band entertainment is definitely tippable! Everyone is a friend at Captain Tony's, and only wish the walls would talk. From Hemingway to Jimmy Buffett, and many others, they all had stories to tell about Captain Tony. From dollars on the wall, to the row of bra's, it all adds to the vibe and the history of this iconic saloon. Always a must stop for us!!! read more

Captain Tony's Saloon - Dive Bars Near Me - Key West, Florida

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I was so excited to get here and see all their stools of the famous icons who once sat on them. There is something truly magical about visiting a place that so many people you love have been in and loved too. The mojitos were some of the best we had! The only thing that could've been improved was the service. It seemed that both people we dealt with had been working in the service industry too long and were very tired of it. They were nice enough and waited on us but I felt like a bother to both and that's not the most welcoming feeling. That aside, this historic Key West staple is obviously worth a stop and a drink! Don't forget to bring a dollar or bra to leave on the wall or ceiling! read more

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If searching out the greatest dive bar and honky tonk then Captain Tony's isn't to be missed! The stained dollar bills covering the ceiling, the lingering smell of old tobacco smoke, bras hanging from the old ceiling rafters, photos of famous visitors and nostalgic signs are just a few things that round out the old Key West ambience! Jimmy Buffett has played here, too. On this beautiful, noon-time April day quite good live music is entertaining those bellied up to the bar, passerbys and actually pulled us into the bar to explore! The beer is cold, flowing and the service on top of a good time. Some fun facts: *The owner was the mayor of Key West *Claims to be the original Sloppy Joe's *Pool tables -2 *Small Arcade here read more

Captain Tony's Saloon - Jimmy Buffett played here - Dive Bars Near Me - Key West, Florida

The best and most awesome dive bar in Key West. Ghosts agree! No food is served here (because I mean, who would eat in this place?) but from personal experience I can tell you the beer is cold, good selection, and the dude behind the bar had a great sense of humor. You'll get music, fun, drunk...that's why you're there, right? Try it! read more

This place was a freaking blast - very cool decor, and a really interesting history that we learned about while taking a ghost tour of the downtown area! I didn't order anything special when it comes to drinks so I can't comment too much on their beverages, but the souvenir cup is fun and a beer is a beer. Live music was great too. Will definitely be visiting again, probably the coolest bar we went to on the island. read more

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I wish there were more bars: - Built around old gallows trees - In buildings that used to be morgues - That have human skeletons as mascots - Which feature real shrunken heads on display - Serving mystery grog in souvenir cups - With barstools dedicated to legendary musicians 13/10. Just go. My macabre heart is so happy. read more

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We stopped in after the Jimmy Buffett parade for a drink~ The bartenders were Great! So fun and funny The live music was an added bonus... So much history to see here A must go! read more

Captain Tony's Saloon - Dive Bars Near Me - Key West, Florida

I liked the vibe here. The live musicians were chill and very good. The drinks were strong, and the clientele was a nice mix of tourist and locals. My one critique would be the price of the bar games (like skeeball). It was way too high. But now I know for future. read more

Great place for the typical dive bar. Cold beer and friendly service. Lots of folks in here. Always room it seem read more

Captain Tony's Saloon - One of two stages - Dive Bars Near Me - Key West, Florida

Captain Tony's is our favorite dive bar in Key West. The pirates punch and the live music should not be missed. You can try your hand at tossing a quarter in the fish's mouth, on their sign. Lots of history in Captain Tony's. Ask about the story of the big tree that grows thru the building. read more

Dark, laidback, and friendly. The Pirate's Punch is some kind of nuclear yellow, fruity drink (not a slushy) that goes down very easily. They've got an excellent gift shop inside the bar that really can't be beat. Don't forget to try and get a quarter into the fish's mouth high above and outside the entrance. It's extremely difficult but I saw it done. One of the better bars anywhere. read more

Captain Tony's Saloon - Pirate's Punch in the souvenir cup. Get a quarter into the fish's mouth and have good luck for eternity. - Dive Bars Near Me - Key West, Florida

Service was good and staff were polite and efficient.... The bar is very dark and the floor is uneven and slanted in places. I walk with a leg brace and almost went down twice. As far as the vibe and drinks it was cool but the facility itself was a significant issue for me. read more

I went down to Captain Tony's to get out of the heat. IYKYK. We love dive bars and Jimmy. Sail on sailor. read more

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Excellent atmosphere and Jimmy the bartender deserves a double tip. Sit at the bar and enjoy yourself. Love this place.

I've been to a number of Saloons in Florida that claim to be the oldest, I doubt if anyone can say with certainty who truly owns the bragging rights. I've been to Captain Tony's a number of time and it consistently rates as one of the dirtiest, my drink of choice here comes in a bottle or can. Everyone should experience this place once, its age alone makes it nostalgic and no one is going to challenge the fact that it's definitely a Key West Landmark. I love dive bars but this one is not a place I want to hang out in for hours or visit the men's room. A lot of the bars in town offer exceptional people watching opportunities being they're open to the street and the tourists traffic, all the seats here are good because the show is on the inside people tend to let their hair down and get a little uninhibited. It's likely one of the stories you repeat often after returning home from the Keys will include this place if you stay in here long enough at the very least it's a photo op... read more

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Oldest bar. For some that makes it worth a visit. They also do have supercheap domestic beers. The one thing that I've noticed in Key West is that you will pay anywhere from eight to $12 for a single beer. They have several domestics for five dollars a can which is nice. I think for nostalgia it is cool, because there are thousands and thousands of dollar bills taped all over the walls and bras hanging from the ceiling. I wasn't in love with it. The restroom was absolutely disgusting and not cared for or being kept clean. So don't think you're going to use the facilities when you're here. Also, they allow smoking inside so you're sitting there trying to drink the beer that you just bought and someone is smoking next to you and I'm just too old for that at this point in my life. Also it's very dark and the floor is uneven so watch where you're stepping because I do think that it's a fall hazard. read more

My favorite bar in keywest. This place has an interesting history. Its one of the oldest bars in keywest and their is a live tree in the middle of the place. Supposedly the tree was used to hang people many years ago. Also people were buried under the floor inside this place. They always have a great musician playing music here. One of the best things is that this place is air conditioned! When you walk in right next to the bar is an AC vent i like to stand under. And its got a perfect view of the live music right under the vent. Drinks are stiff here but they arent the cheapest. Capt tonysbis the quintessential keywest bar! Its a must see when youre in town read more

Captain Tony's Saloon - The AC vent i love - Dive Bars Near Me - Key West, Florida

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This place is a key west institution. Full of history and good times! There's pool tables, skee ball, and live music. Drinks were strong but delicious. read more

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Awesome place with loads of history. Always stop when we go to Key West. Off of Duval but not far.

Local dive bar good drinks and if your a jimmy buffet fan is a must stop and have at least one drink. Not a place I would just sit and drink in but fun to be in for awhile until you move to the next place. Good drinks cool old key west vibe read more

It's hard to be a parrothead, and come to Key West and not go to Captain Tony's, given all the songs and references Jimmy Buffett made to Tony and his bar. I'd say the bar definitely has a kind of funky vibe, but it's ok. Dark and smoky, for sure. Place was pretty busy for being an afternoon. But was able to get served at end of the bar and had a beer. All in all it was cool to see the memorabilia there. Just bear in mind if you don't like cigarette/cigar smoke, you'll probably not stay long. read more

Best iconic bar in key west. Miss captain Tony he was an amazing guy .. a true icon in key west

Ordered a tee shirt from this place on may 30th 2025 . They took my money processed the card and never sent the shirt! 3 attempts to contact by email and phone no one answered! If this is how you do business for a tee shirt! I'd steer clear of anything else ! Still waiting ! read more

A must place to visit in Key West even if you're not a drunk. We purchased many items from the Bar store for gifts prior to having a drink. Great service. Will return. read more

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Great place to hang out, shoot the shit with a game of pool and get obliterated all day long. read more

Captain Tony's Saloon - Dive Bars Near Me - Key West, Florida

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Worst service ever! Only 1 bartender that was also the bar back. Waited 20 mins at the bar, never got to order a drink. Left.

Service was great friendly and quick! Ambiance was fun and very much an iconic place to visit. read more

Captain Tony's Saloon - Sign outside - Dive Bars Near Me - Key West, Florida

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