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.

As someone visiting from up north, this place instantly felt like one of those spots you wish you…read morehad back home. The Dive Bar Shirt Club has the kind of laid-back, no-frills vibe that feels like hanging out in your best friend's backyard--the one who somehow has all the toys, great music, and everyone ends up there without planning it. The ambience is pure Florida Keys: relaxed, fun, and welcoming, like you're part of the crew the second you walk in. Then there are the tacos... easily some of the best tacos in the Keys. Fresh, flavorful, and exactly what you want with a cold drink in hand. On top of that, the prices are more than fair, and the selection--drinks, merch, food, all of it--is absolutely top tier. It's the kind of place that makes you understand why people never leave the Keys... and why visitors like me keep coming back. Here's my breakdown Food 5/5 Location 5/5 Price 5/5 The foodie ninja shall return

Coolest place ever. Bar and liquor store all in one. Open till 2am Friday and sat. Live music…read moreDrinks made fresh. Cool atmosphere. Sand floors

Walk up window to solo bartender serving quick and delicious drinks. The Pain Killer I had was…read moresoooo good. Nothing fancy, but they had a live performer a bit after we arrived. Cool island vibes here

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 is a must stop in Key West. It is a small bar that has the most amazing selection of rum. We…read morestopped in for some fun mixed drinks and they did not disappoint. I had a banana frozen rum drink and a mango rum. My husband had a painkiller and a rum runner. Our bartender was friendly and we chatted about places to eat. The gentleman next to us came in and ordered a rum flight. The bartender was able to direct him to some options that fit what he was looking for. It is a great ambience with drinks for any type of rum drinker.

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 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.

Great bar and cool ambiance. They have a lot of inventive cocktails and serve absinthe as well…read more Love their upstairs speakeasy, hinote. They also do live music on the back patio with is more of a dive.

Super friendly and engaging staff. Not a big bar but they had everything we needed. Ordered some…read morefood and the lobster quesadi and wings. Both were delicious and served hot. It has a bay view and we will be back.

Great atmosphere, attentive wait staff, and great food. This was our first dining experience when…read morewe arrived in Key West, and was pretty much the best.

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.

Incredible bar in Key West. If this had been our first stop, we would've hung out there all night…read morelong. Great prices for drinks and super sweet, welcoming staff. You could spend hours admiring the decor. My boyfriend ordered an old fashioned and it was mixed perfectly. Honestly I can't say one negative thing. We both remarked that if we lived in the area, we'd be regulars. Be sure to stop in on your next trip!

Awesome local bar, with lice music and great drinks at a very reasonable price!…read more Walls lined with patches from EMS, fire fighters, Navy, Air Force and police. Plenty of seating inside, but they also have seating outside too. Swing by, and chat with the bartenders, as they've got some good stories to tell.

Outstanding! This is a great little bar with outstanding drinks at a great price point!…read more Max the bartender is an absolute pro. There's always a huge line waiting on him, but he knocks out drinks at a rapid pace. On my list to visit everytime I'm in town.

Great key lime pina colada at this bar. We weren't sure if it would be good since it's a tourist…read morespot but it was blended so well. Best frozen drink of our trip.

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.