We were searching for a fun craft cocktail bar on our pub crawl and we were lucky enough to get a…read moreseat at the bar at General horse play, probably because we went early. The vibe here is cocktail den, cozy, intimate, dark. It's like a sexy little vixen in the cocktail world with an air of mystery. The menu was very creative, I mean unique combos with premium spirits including absinthe and the bartender was helpful in that she would suggest a drink based upon spirits & profile you prefer. We each had a cocktail and Ithey were both delicious. We tried the I pity a fool, which is Jamison whiskey, peach, lemon, and black pepper. Also, El Cuerno de Aire , an Espadin Mezcal, lemon, and blackberry combo. Yum, Next time I'm in Key West I am definitely coming back here. Don't miss out on this one.

Absolutely loved the drinks menu at General Horseplay. I ended up walking over here from our hostel…read morewith a friend after she got in after a late flight. She wanted a cute cocktail with really good atmosphere, so I went to the Internet and found this place! It genuinely was so cute and amazing. We had an awesome conversation with the bartenders and they recommended our drinks for us. Since it was Christmas time most of the drinks Were holiday themed, which I've never seen before. We each had a few drinks, took some really cute pictures with the decor, and went back home to the hostel to catch up. It was a really solid night and I would recommend to anybody in the area.

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 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.

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.

The rum bar is everything you need after a journey into Key West!…read more This quaint establishment sits on Duval street and offers inside and outside seating. Perfectly placed for people watching in the evening and away from the louder bars on duval. The service is exceptional and the mai Thai cocktail I ordered was delicious. A great mix of seating on their patio makes this a must-stop for anyone who enjoys a strong rum themed cocktail!

The Rum? But why the Rum? 'Cause it be DELICIOUS!!!! This place is friggin AWESOME!!!…read more The wife and I are out exploring the Keys for our anniversary, and we happened upon this bar while walking around Key West. First off, nothing says tropics like Rum! The name is all that needs to be said. Nothing more... nothing less. It's a small and it was packed. Elbow to elbow, which says nothing other than you know this place will be good. My wife is especially cuckoo for Cocoa Puffs when it comes to anything Chesney and Blue Chair rums! You had us at Kenny Chesney Island Girl, and we just had to find a spot and enjoy. And we Most certainly did! It was sublime and refreshing. I was even able to walk out with a souvenir Rum Bar hat (purple). Without a doubt, we will be back and we're telling all of our familia and friends of this place! Thank you for the local experience and as always, Enjoy & Happy Drinking!

This place's reputation precedes itself due to the history (I'm sure you already know that it was a…read moreHemingway hangout) so, as you can imagine, it can be busy. We hit it on at the end of the night, for a night-cap beer, and found it to be fun with lots of potential. There wasn't a seat to be hand in the place but we were able to snag an open spot at the bar for one round (very lucky!). The bartender was very inviting and she was FAST with the beers! There was live music on stage, which sounded really good, and the overall vibe of the place was chill (despite the packed house). I could see why people flock here, it's a solid hang out.

A really great bar with a cool history and fun atmosphere. Who wouldn't want to have a drink where…read moreErnest Hemingway used to come back in the day? Each time I have come in here, the live music has been great and the drinks are delicious. The large venue with its high ceilings makes it feel open and airy. They have doors open on the sides which keeps it feeling fresh and not like you are inside. The servers are fast even when busy. The bartenders make great cocktails. They have a nice retail/merchandise store towards the back of the bar/restaurant. Definitely make this a stop during your stay in Key West.

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

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.

The concept here is executed so well - it is one of best finds we have found in years…read more First, the decor and atmosphere is incredible. The decor is seductive in such a tasteful and classy way, everything is so romantic. It's beautiful. Cozy, intimate booths. Sparkling chandeliers flickering in candlelight. Ambient lighting. It is a perfect place to end your evening with your partner. We made reservations the morning of, on a Wednesday evening for our anniversary, and were seated promptly. Service was incredible from start to finish. I appreciate their ipad menus with questions to ask your partner, peruse the menu, and read about the origins. There are plenty of drinks and deserts with double entendre names, they're so fun. Huge positive that they have virgin drinks, and several to choose from. Both deserts we tried were out of the world delicious. The missionary crisp ice cream and flavor was 10/10, no notes to improve. Key lime from behind was the best key lime I've had in my life and quickly became the best we have tried on Key West. Incredible and what a lovely place!!

Well, no it isn't…read more But our party of five enjoyed having drinks and dessert here. It's really more aimed at a young couple in love, but we had fun. Romantic lighting and private booths made for some good ambiance. The iPad menus were great and very useful in selecting desserts and drinks. Everything on order is accompanied by a double entendre title, which makes it fun to pick. Candy rimmed beer was good; and the berry crisp and ice cream offerings were tasty. Honestly too big, even for two. But they were trying to do something different. To know: they do not have a license for hard liquor. A fun spot to have a sweet treat. Maybe don't bring the kids.

The location is awesome, a balcony above Duval Street, right in the middle of the Key West action…read more If you only want basic beer or wine, *maybe* you'll enjoy yourself. They offer a *very* limited choice of cocktails, and couldn't even make a daiquiri for us. Bizarre. The bartender suggested we go to another bar with a better choice of cocktails, so we did. BTW, they only serve drinks in plastic cups, like a pool bar, if that matters to you. Halo is located in an expensive upscale hotel, but this is definitely not a high end experience.

While staying at The Saint we stopped in here a few nights. They offer live music at this rooftop…read morebar. They also offer more basic drinks, like a spirit and a mixer or beer. The bartenders are friendly and the music was really good. The view of Duval below is definitely great... makes for excellent people watching! Definitely recommend stopping in!