21 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.“

“Celebrated my 30th birthday here and it was by far the best food we ate in Key West. We ordered the Asiago bread and squid for our appetizers. The squid was FABULOUS!!! I’ve been craving it since! For dinner we did the wahoo, swordfish, prime rib and chicken. All of which we were each raving about to each other! The atmosphere was dimmed candle lit tables and our server was great! Highly recommend for anyone wanting to taste high end food and it be up to par! Will definitely be back!“

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

“Unfortunately the seaweed had come in and was pulled up on the beach, so the stench took away from the ambiance. Plus there was a large party who thought the entire place was theirs. Food on the other hand was really good. Would come back when the seaweed isn't so bad“

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

“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“

“Wonderful time. Great happy hour!“

“great food, good prices. beautiful view“

“Perfect location on Duval! Easy walk to beach, bars, and restaurants. Extremely friendly and helpful staff. Rooms have everything you need, refrigerator, microwave, toaster, beach chairs, beach towels, information on local attractions, I could go on and on… Oh and the fact that the rum bar is right downstairs is very convenient, maybe too convenient, lol! 🍹🥴“

“I love this bar! Very laid back, staff is awesome, and a great place to just hang out.“

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

“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!!“

“I love this bar! Very laid back, staff is awesome, and a great place to just hang out.“

“Best place in Key West for dinner and cocktails“

“My husband and I have been coming here for years. It’s exceptional. We never have any problems with dietary restrictions and the service is 10/10“

“This place is incredible!“

“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!“

“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 really enjoyed our time at First Flight, from the atmosphere to the food! But we especially enjoyed the service. Lorena was wonderful—attentive, personable and a joy to interact with. The conch fritters were good, as were the steak tacos, tropical salad, and swordfish. A varied menu with reasonable prices.“

“Oh my gosh! Best place ever! Amazing oysters and amazing buffalo shrimp. But most of all the service! Wells was our waitress and she was AMAZING!!! Thank you for making our experience wonderful!!!“