22 Best Cocktail Bars in Key West

“Only in Key West. A dive bar with a resort built around it. Have not stayed at the Pier House Resort, but the Chart Room is definitely worth a visit. Very old school KW, surrounded by very new school KW. This is where Jimmy Buffett 1st stopped upon arriving in KW (allegedly) and played for the likes of Hunter S. Thompson and Jim Croce. This is where Mel Fisher charted his days searching for the shipwrecked Atocha (at the round table in the back). This is where Tennessee Williams and Truman Capote wet their whistle (but not at the same time). This is where the Pirate Who Looked at Forty Philip Clark tended bar. This is where David Allan Coe was inspired by poet Shel Silverstein. This is where famous and not-so-famous regulars have their ashes interred in the bar (seriously, look for the corks). Most of Key West's history is embellishments and outright BS, and this awesome bar fits right in.“

“Best seafood dinner I’ve had since 2005 hands down. That’s how good it was‼️The wife and I are in town for our Lucky 13yr anniversary and we were debating between dinner establishments. We settled on this one because it was in close walking distance of Casa. Dinner did not disappoint.“

“We were guests for dinner and very happy with our choice., The cocktails were superb and our meal very good. Probably not a,ways easy to get in but this was a Sunday in September and it was not too busy. This is outside under cover with a very relaxed atmosphere out by tge beach bar. This was what we were looking for. This is Key West after all. Kt Venice fl“

“Bartender alone ! She made an Outstanding Old Fashion and grapefruit Martini.“

“This is a joint, a bar, a saloon, a gin mill, locals kinda dive bar where folks get together, play pool , drink, catch up with one another open until 4 am. My kind of place. I'm a traveler (not tourist) visiting America at ground level in my RV. As I travel I enjoy really experiencing where I'm at . I do some culture things , well down here this trip by didn't get to go scuba diving because of sinus but I did finally manage to catch the red-headed stranger and after Willie Nelson did his thing I went looking for local flavor. And this is truly one of those. I've talked to I talked to locals there could have been coming for more than a couple of decades I think as it's been under different names. They allow smoking and indeed many of the denizens had one sticking out of their mouth at some point during the night. I met an absolutely Splendid wonderful Grand d a m e who introduced herself as Tootie and described herself as a barfly. Such an understatement even as wonderful as that word is she was one of the finest bar flies I've ever met. She was rail thin her main diet Aid being camel non filters . Wise , soulful , full of good cheer and humor the kind of lady that gives a certain middle class blue collar Elegance to a local Watering Hole. We started talking about her cigarettes which I hadn't seen in a while and she offered me one. I've been more than 20 years without smoking and I appreciated the offer but I declined. I don't personally partake anymore but I don't believe the government really belongs in the bedroom, The Gin Mill or our freaking pocketbooks. Life in America is about choices. You find what fits and you go there. I really felt right at home there even though I wasn't part of the crowd people were friendly within their own sphere of influence bar stool to Barstool and a few made casual inquiries which I answered politely with the joy being able to bask in another areas Public House. Man I really love that place. I forget the current name because I mispronounced the old name Shimp Daddy's (as shrimp) that Tootie spent two cigarettes trying to school my out of town ears to drop that R in there and then she told me some of the history and that's why I had gone there. God Bless America and every bar or other establishment like this all over. It's a great place to go in, sit down, shut up and listen to Key West. Good night tooty“

“Excellent drink / bourbon selection. Nice speakeasy decor and feel.“

“Wonderful time. Great happy hour!“

“A great place for music and drinks!!!“

“great food, good prices. beautiful view“

“Spent the night there last night. Raymond and Mark are wonderful gentlemen! The place is beautiful, staff very welcoming, and the drinks were delicious!“

“Best dinner on the island! Four of us luckily got a late reservation on a rainy Christmas evening (2023). Food was fabulous! Service top-notch. Great atmosphere. Nice specials were offered for a holiday dinner.“

“Ok, so just for perspective, we are usually here during Fantasy Fest. Today, we came on a cruise ship. Visited our favorite place for a couple of drinks. SAVANAH WAS GREAT!!! Give her a raise. I mentioned to her that was the cleanest I have ever seen their bathrooms. We had a laugh when I explained when we are normally here. LOVE FAT TUESDAYS!! The new Key Lime Colada is a MUST!!“

“Great cuisine and great drinks . Always the best live entertainment on the Island !“

“amazing performances by artists“

“We had some friends in town and they found this spot on Google. We showed up later in the night and everything had to be ordered through the bar, which wasn't a problem for us. The bartender was very friendly and ended up serving our table. Very nice and informative. The Oyster Rockefeller is probably one of the best I have ever eaten along with the espresso Martini!

I have since recommended this place to anyone who traveling to the keys and cannot wait to return there this winter!“

“We ate dinner here in December 2023…we had bruschetta, soup, salads and my entree was the steak with peppercorn cream sauce….ive never tasted anything more delicious in my life! If I could give this restaurant a million stars I would! All of the food was absolutely delicious and the atmosphere was spot on for couples night out!! We are looking forward to coming back!“

“A great place for music and drinks!!!“

“The cutest Tiki Bar Restaurant of all the hotels in KW! Best drinks and snacks when hanging around the pool! Jennifer and Milly are absolute Queens ?? with making drinks! They can help you with anything you need! I even tried taking them home with me ??‍♀️ I can't wait to come back! ?“

“Romantic dining with the most creative entrees . Such a memorable experience“

“We visited the restaurant last week it was full of people and believed that they were short of staff.
The host was the best! She was fast and kind and gave us a great table to enjoy our dinner.
The server was also nice and answered all our requests. The drinks were bad and the food was a meh, the oyster were good but the fried calamari were bad. I don’t know, in general I was waiting for something better, but the experience was OK.“

“Try the whole yellow snapper, it's great! Crispy outside, meat fell off without bones. The vegetables were fresh and seasoned well. My husband tried the fried peanut butter and jelly sandwich. He did not complain, exactly what he expected.“

“We were guests for dinner and very happy with our choice., The cocktails were superb and our meal very good. Probably not a,ways easy to get in but this was a Sunday in September and it was not too busy. This is outside under cover with a very relaxed atmosphere out by tge beach bar. This was what we were looking for. This is Key West after all. Kt Venice fl“