Interesting bar complete with a hanging tree and some tombstones right in the middle of it all. Haunted as hell and rich with history. I was very creeped out and I didn't stay very long. The staff was kinda crass, the music blaring and there's a heavy vibe happening. Some people like that, though. I'll pass. Worth at least checking out. read more

Captain Tony's Saloon - Bras, money, hanging tree and death! - Dive Bars Near Me - Key West, Florida

for all the people leaving negative reviews on Captain Tony's don't go there because you don't get it and we don't need you in there really I've been going there since the late 80s and the place hasn't changed that's the whole point. It's a dive bar when there's a singular guitar player sitting on a stool and you drinking 16 ounce tap beer out of a plastic cup that's a little bit of Key West heaven go down the street to Wendy's or go shopping crocs if you want to have a boring time that's your choice. I hate that everything has to change into a TGI Fridays read more

What a great and chill bar! We were visiting the Key West for my friends birthday party. Due to Covid19 are options were limited, however luckily restrictions were lifted slightly so we were able to to enjoy drinks without the pains of ordering food and wearing a mask. Upon being seated you're good to order drinks from the bar. We gave a credit card and opened a tab for our large group. The drinks were well balanced, we were not ordering anything out of the ordinary... Vodka and Tequila with soda water and scotch on the rocks. There was a live band playing as well which were quite good, oldies all night long. We had a great time! read more

My husband loved the money on the roof. I always enjoy playing the old-style bar games. A great place to hang out at night. read more

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Your average Key West watering hole, nothing fancy or special. A grand mix or locals and tourists.

I can't explain how awesome this place is!! We went two nights in a row. The bouncer and owner made us feel like we we're at home. We met the owner and he is the nicest person ever!! We walked the entire night with him and he even asked us to return the following tonight so he could share some old pictures with us! We returned the following night and when he saw us, he came straight up to us and shared some great stories. We even ran into the bouncer during the day and he was so friendly! If I return to Key West, I will always always go here just to hang out with Joey! read more

Live music! Tasty pirates punch. And my favorite- skeeball! Came here in the afternoon for a cocktail and the weather was perfect and they had a musician. Bras and $1 bills all over the walls. Lots to look at! read more

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

A Key West dive. The stories that place could tell! Lots of bras!! Although I didn't see any ladies taking any off- and I begged all of them. My much younger companion was not as amused as me. read more

Captain Tony's Saloon - Bras- some big and some not so big. - Dive Bars Near Me - Key West, Florida

Even when they're not busy bartenders may overlook you if you're not gay. Plus, really bad live music there.

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. read more

Captain Tony's Saloon - After our big day tying the knot!! - Dive Bars Near Me - Key West, Florida

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A true dive sports bar. It's an institution and a must do for any bar crawl in KW. You can donate $bills and bras to the wall and ceiling collection if inclined. It's kept authenticity unlike lots of bars. It's on Green St. Near Rick's. Look for the big grouper. This is where KW Sloppy Joe's used to be before their current location on Duval. The real original SJ is in Havana and nothing like the one on KW. read more

This place is dark, divey, and has some vibes. I don't know if they are "good vibes" per se, but it has personality... maybe that's why Hemingway used to come here back in the day? (Yes, THIS is the original site of Sloppy Joe's, not the new location that now has that name) Didn't try the drinks, but they have a custom-brewed amber ale on tap. The live music was pretty decent. read more

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

Grumpy bartender. The place is infested with ravenous fleas! We were already leaving, but the bugs drove us out even faster. Did not even finish our drinks. Literally had to go to CVS and get Benadryl. read more

So much fun! The original Sloppy Joes and where Jimmy Buffet got his start. The decor -- dollar bills and bras-- adds to the relaxed island vibe. Live music, no cover. read more

Best bar in Key West, extremely friendly crew and a place that is truly a piece of Florida history. Found myself in here just about every night while in KW. Thank you for an incredible experience! read more

We didn't eat, but we did buy shirts after hearing the hilarious history of Tony's from the sales man. Drinks were cold and service was quick. Great music. This place is one of the oldest in Key West and supposedly frequented by celebrities when in town. read more

After coming to Key West 3 times, I finally learned the story about the "original" Sloppy Joes so I knew I had to visit here. As you could picture, it was definitely a dive-ish bar with a lot of local feel. It was dark and one guy was jamming on the guitar. We came by on a Sunday night so it was probably not at it's normal capacity but bartenders were decently nice and prices were fairly cheap. The most exciting thing was all the history about Tony and looking at all his pictures and articles about him. Not my vibe with all the bras and dollars and dark dingy. I felt out of place and was getting stared at. The bathroom was extremely old and not super clean but comes with the territory. Definitely worth a stop but not my new watering hole. read more

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

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Bartenders were extremely rude. The place was lifeless with a bunch of snotty college kids. The one man band stunk. There were a bunch of idiots out front throwing coins at the sign. Did I mention the bartenders are complete a**holes?! Do not waste your time here. There are plenty of other options in Key West. read more

Punch Bowls Captain Tony's Saloon is as unique as Capt. Tony himself. Built in 1852 Capt. Tony's is the oldest bar in Key West and was the initial location of Sloppy Joe's. Originally, Capt. Tony's was built as a the island first morgue and used as an ice house. Reportedly the coroner buried his daughter under the floor on the bar which is now the pool room. There is also a tree growing inside the bar for those who want to "hang around". It's a must stop for Parrot Heads. Tip: Grab a punch bowl and roam the streets, you'll get drunk. Thanks read more

Loved this little dive bar. Get the hurricanes for 10 bucks and start the night off right. Good live music inside not too loud. Bartenders very nice and courteous. Def recommend stopping in for a drink. read more

This is one place you should come while in Key West. Captain Tony has a legacy a mile long. Many famous musicians and Movie Stars came here. You never know who you will see here. Ladies if you dare, you can hang your Bra in the rafters, Oh yes you have to sign it also. The band was OK when we were there. Good dance floor and bar. The service is OK, the place was packed when we went there. Lots of history on the walls with different famous people with Captain Tony. It is a Key West Must to do, if you drink or not. visit captain Tony's, I am sure you will be glad you did. I sure was, what I can remember of it. read more

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

Any time I've come to Key West -- which is going back to when I was a student at the U, I've had to make a stop at Captain Tony's. It's almost like a pilgrimage when you go to some of these bars because they're part of the Key West fabric -- especially, when we're talking about their night life. While most first timers and people that are close enough to make the two-to-four hour drive from South Florida/West Florida (depending on where you live) will go to Sloppy Joe's, you are better off checking out Captain Tony's first for a few reasons. Historically, it is the original location of Sloppy Joe's in the 1930s before moving to its now-famous location on Duval St -- Hemingway used to have drinks there in its original carnation. The bar is built around a large tree, which, believe it or not, was the town hanging tree for pirates. Since the 1800s, the building has seen itself used as a morgue, speakeasy, bordello, amongst other things -- the morgue part is especially true as there were remains of at least 15 people buried underneath the floor boards of the bar. It's a place that was once Hemingway's place to have a drink. Besides all the historical and macabre reasons to at least check out the building, the bar retains a ton of character today between the walls and ceilings covered in dollar bills, bras, license plates amongst other artifacts. It's definitely a place to include on a bar crawl as you get increasingly drunk through the streets of Key West. The live music always fits the mood once you're there -- and by mood, I mean drunk, tipsy, or at least having a good time. The beer is cold and the cocktail flow nicely. Usually any time I'm there, I'm by the stage area checking out whoever is playing. They have pool tables to rack a few games while you're at it. The saloon is also a good place like many in the area to people watch and hang out at any time of the day. So whether it's your first time or your tenth time, make sure you check out Captain Tony's. It has lots of character, and its share of them. read more

Heard this was a must see in the Keys. Went in, sat at a little dingy table and then moved up to two seats at the bar. Place very dark and dreary. After about 10 minutes and neither one of the two bartenders ever acknowledged us, we left and went to Sloppy Joes and sat at a bar and had a couple of beers and extremely nice service by two bartenders read more

Good music but just gross inside. Go at night when you can't see the dust n grime. I went during the day. read more

Absolutely one of the places you need to go when you are in Key West! Iconic, fun and plenty of libations available! read more

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

Quick visit for a drink on a Wednesday afternoon. As pictured it's chock full of vibe. Drinks were ok. Expectations were met. Bartender and fellow patrons were friendly. No real complaints - average so it gets a 3 read more

Great music and cold beer. The bar tenders kept Capt Tony's Amber flowing. Great JB tunes and chill Key West vibes. No food.

The place smells like smoke. It's not fraternity house party room filthy. But the darkness and smoke smell had me walk through and leave. I like the story and wish I could get word to mgmt on how to change. Next I walked over to Sloppy Joes and found a clean table right away. It was crowded for sure.I left before getting service... on the SJ review. read more

This review is based only on this bar's appeal as a fun dive bar and not as a place to eat (I honestly don't even know if they serve food). It's got a long history and is a staple of the Key West dive bar portfolio. If you like dive bars it's great. It's one of those places with hundreds (if not thousands) of dollar bills stapled to the ceiling and beams and has a quirky sort of layout with little nooks and crannies where you can play bar games and there is live music. The bartender the day we went (middle of the day on a Monday) wasn't particularly the friendliest chap on the island but it was still a great place to come have a couple of beers and listen to music. The bottom line: If you like historic dive bars and live music, this place is great. read more

Captain Tony's never disappoints. The live music is always on point, and it's all day. The bartenders go above and beyond to take care of customers. Drinks were great and flowing. I've been coming to captain Tony's for over 6 years now, and service has consistently been good. They also sell there own beer. Captain Tony's amber ale is flavorful and the pricing is fantastic. read more

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

Best old bar in the keys. Been drinking in this bar for 40 years and remember Capt. Tony well!

This place is awesome! If I lived in Key West, this might be my regular watering hole. The entire ceiling and posts are COVERED in money. Also hanging from the ceiling is bras. I think most of the women who go to this bar, leave their bra behind. I happened to have just bought a new one so I did not leave mine behind. I believe they have live music every night which is a bonus. We stopped in here 3 nights in a row and every one of the bartenders (all males) were some of the best bartenders ever. They were quick to get your order, give you your drink and get your change back to you. The live music was such a bonus while we were there. They do have a pool table and a couple of arcade games if you're not looking to just sit at the bar and listen to music. I have to say the women's bathroom is THE WORST I'VE EVER SEEN!!!! Some very irresponsible women had been in there and didn't flush, urine on the seats, left tampons on the floor, the garbage's were overflowing, there was no paper towel to dry your hands and just all around needed to be renovated because it is in very rough shape. I'm totally ok with the rest of the bar looking and feeling very old and divey. But at least give me a decent place to pee while I'm there. This might be a tourist trap but I loved it. Go here at least once. read more

Great spot some of the "locals" took us too...a little loud and dark but a fun place! Tradition: Toss quarters in the fish's mouth for good luck! read more

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

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If in Key West definitely need to visit here to soak in some history. This is proclaimed as the oldest bar in Florida circa 1851. Famous for being Hemingway's hangout spot when in the Keys. Don't be fooled and go to Sloppy Joes on Duval. This is the real place chase true Hemingway history. Inside is dark and dimly lit (no windows) The inside of the bar is covered in dollar bills. Live music was a plus and they have pool tables. You'd think the money posted everywhere would be the strangest but I think the tree growing through the bar was the coolest. read more

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Service was great and drinks tasted fresh. Bands were nice. Best part was I was joking with the cocktail server about needing another drink in 13:27 minutes.... She was back at 13:02 to take my order and I had it in 13:27! This is a must stop! read more

Loved the atmosphere! It was so fun adding a dollar to the wall! I look forward to visiting in a few years to see if it's still there!

I love the tree and the grave stone that are inside along with the history of the saloon. It is a neat place to check out while in the area. The drinks are decent priced but there is barely any alcohol in them when you order. This is the most talked about saloon on the island since Tony was the mayor. Again a neat place to check out and look inside but maybe skip the drinks. read more

Hanging tree in bar. 2 pool tables with head stone underneath (Alvira). Suppose to be (15) bodies under floor. Bras & money taped to ceiling & walls. Great drinks. Great music. I get toasted here. read more

Best mojitos I've had in years even if they were served in a plastic cup! Interesting place with lots of history and characters to match! read more

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