I stopped by Captain Tony's Saloon and it was such a fun, classic Key West experience…read more 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.

We were with friends from CO who were visiting Key West for the first time. After walking around…read moreMallory 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.

Drinks and flatbreads were great. Pretty affordable. We were there during the day so didn't get to…read moresee the bar in full swing but enjoyed it. It is a flight upstairs as an fyi.

We stopped into Surly Siren Saloon for a few drinks and had a fantastic time. The atmosphere is…read moreexactly what you want in Key West--laid back, unique, and full of character. The drinks were well-made, and the service was friendly and quick. It's a great spot to duck into for a few beverages and soak up the local vibe. We'll definitely be back

While roaming around Old Town we stopped in here on a recommendation from a local. He said it's his…read morefavorite spot on the island. It's a dive bar through and through but I happen to be a big fan of dive bars! However, this one fell flat on it's face with the service. I wouldn't say the place was packed but there were not any open seats at the bar. I posted up the best I could but for the better part of 15 minutes both bartenders didn't even come to my side of the bar. I then moved to the other side and waited another 10 minutes to be served (at which point the bartender said "Didn't I just serve you?" Um, no, you most definitely did not. This place has two saving graces: 1) A water jug full of cold water for the taking, off in the corner. Love that. 2) A popcorn machine that had DELICIOUS popcorn! YES. If you can manage to get a beverage then I think you won't mind Green Parrot's (very) relaxed atmosphere and delightful little perks. My takeaway is for the staff to mix in some work to go along with their chatting with the regulars...

I found this to be a great classic place to hang out. Good live music, a lively crowd with a mix of…read morelocals and tourists. They have a great beer selection (including Lagunitas IPA from California, WTF?), good service...what's not to like? The location is a reasonable walk from the cruise ships too. Plus, there are pool tables and a dart board and free popcorn. This will be a definite stop the next time I'm down there.

We stopped by on way to room... A great vibe! I see why Jimmy Buffett came here!!…read more Had a watermelon margarita! Was great! Kudos to the great bartender!!!

This place is a hidden gem. The oldest bar with character. Free popcorn peanuts and hot dogs ( if…read moreyou dare). ) lots of items adorn the dark walls we even met a friendly pooch. A fun find that we know as our secret bar has been revealed

Limited food, tacos are the specialty. Beer and wine only. Two for one happy hour. Service is…read moreexcellent. They use logo aluminum cups, ask nice they might give you one. Nice place, lots of old vinyl covers for decorations. Very comfortable setting. Puzzles, games for fun. Ladies, beware the restroom temptation. Enjoyed my time there, will return

A night at Shirt Club is less about going out for drinks and more about embracing whatever strange,…read moremagical chaos the island decides to throw your way. This is a true dive bar in the best sense--dark, loud, unapologetically weird, and absolutely unforgettable. The drinks flow, the stories blur, and at some point you realize you're no longer entirely sure how you ended up where you are... but you're fine with it. Now. The ladies' room. If you know, you know. Let's just say there was a handsome fellow, a conch shell, and an air of mystery that felt very on-brand for Key West. Details are intentionally vague--some things are better left unexplained--but whatever was happening worked. Worked very well. My nieces? They fell for it hook, line, and sinker. Completely enchanted. Equal parts confused and delighted. A core memory was made, whether they asked for it or not. Shirt Club is the kind of place where stories are born, logic is optional, and you leave with inside jokes you can't fully explain to anyone who wasn't there. It's chaotic, hilarious, and 100% Key West. Would we go back? Absolutely. Would we ever expect to understand everything that happens there? Not a chance -- and that's exactly the point.

Cool place. Great atmosphere…read more Drinks were excellent as was the appetizers. Live music.

Great service Clean…read more Make sure you get a tee shirt Cliff Cody is awesome Good food Handicap accessible

Good for 1 or 2 drinks and that's it.Pay cash ,if not you might get overcharged if paying with a…read morecredit card. Thats all I have to say about this place ! Not for me, however you have to experience it at least 1 time . However the amount I was overcharged was reversed same day.

The Bull and Whistle Pub is one of the places that must be checked off your list when visiting Key…read moreWest.  There are three floors, with live music regularly on the first floor. The second floor was our preferred spot as it was less crowded and you could sit out on the large narrow balcony and people watch over Duval St.  The bartender we had was amazing! My wife's standard bourbon and diet coke was spot on and way better than some of the watered down drinks served at other places. Good selection of draft beer. The happy hour "well-drink" special was one of the best around.  Laid back with an everyone welcomed vibe.

A fun little bar to stop at! We stopped by twice on a recent trip to the Keys and had the same…read morebartender both times. He was super nice. The place is very tiny (truly the smallest bar). Probably enough room for two people to order something and then anyone else would have to wait more toward the sidewalk. It's still fun to stop by and say you went!

The name and the size of this bar lures you in- as long as there is space!…read moreWe popped in so our group could do a shot-ski. The bartender made key lime shots for this occasion and they were delicious!

We had a few birthday celebrations in our group, so we decided to stop into Tiki House for drinks…read moreand a little dancing. The vibe for an early Friday afternoon was really good. The DJ was playing some great music that kept the dance floor going, and the bartender did a solid job keeping up with orders and taking care of everyone quickly. No complaints from our group at all. Everyone had a great time, and we'll definitely be back next time we're in the area.

I've been wanting to go to the newly relocated Tiki House and managed to go on a Thursday night,…read moreand the atmosphere was exactly what you'd expect from a Keys tiki bar--laid-back, tropical, and full of energy. The live music was a nice touch, and the setting definitely screams vacation mode. However, here's the catch: Happy Hour was advertised everywhere--on the front signage and even in the hallways--but when we asked about it, the staff seemed completely unaware. No one could confirm the specials, and it felt awkward having to explain what we saw posted. For a place that promotes Happy Hour so visibly, this was a big miss. Drinks were solid, and the vibe was fun, but that disconnect on Happy Hour left us feeling a little disappointed. If you're going for the ambiance and a good time, you'll enjoy it.

Friends said the food from the truck was awesome. It's a great little place with live music and you…read morecan hang out and talk and relax. Not a super clubby environment it's laid back and great. The music the day we were there was superb. It was a female I didn't catch her name but she was top notch. Matteo was our server and he was a hoot!! We had the best time. Thanks

We stopped here to take in a live musical performance by talented guitar player and singer, Noah…read more We were semi-covered beneath multiple sailcloth strung above us, but still able to see plenty of stars and an enormous bright moon between the gaps. Beer was cold and the crowd was having a great time. A food truck, Garbo's, is also on site to order fantastic food.