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    Pineapple Bar

    4.3 (3 reviews)
    PriceyCocktail Bars
    Closed 11:00 am - 6:00 pm

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    1 month ago

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    11 years ago

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    10 years ago

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    The Roost

    The Roost

    (111 reviews)

    $$

    This bar is so incredible, we came three times during our trip! It sounds like a dive bar but it's…read moreactually an upscale craft cocktail bar. Loved their porch sipper and the Sazerac. Black manhattan, rosemary gin and tonic, and blowing smoke up your glass were great too. Service was great and loved the decor. Stumbled upon it walking around and saw the menu, and had to check it out.

    The Roost is one of those super cool artsy intimate neighborhood pubs that you feel lucky to wander…read moreinto. And it's not only the drink menu with its custom crafted cocktails, wines, beers & ciders that will wow you but the accompanying snacks and bites are just as divine. And bonus, it's not only a bar, but also a liquor store with an awesome selection of wines and spirits. This bar definitely has a locals vibe. It's small , dark and cozy and the small tables with velvet chairs are very welcoming. We loved it so much. We came back for a second night. We tried the Maria Rita, which was a reposado tequila with fresh lemon, lime, hibiscus, and habanero, perfect version of a margarita. We also tried blowing smoke up your glass, this was made with Papa Pilar, dark rum, pineapple, fresh lime, house made basil syrup & tiki bitters. Absolutely fabulous. We also tried their deviled eggs each topped with unique toppings like trout row, bacon, and scallions. They were absolutely fabulous. They also have a great selection of charcuterie, Key nuts which you can order with different flavor, profiles, caviar, olives & peppers. Also, the most generous happy hour I've ever heard of from 12 to 6 PM every day. Don't miss out on this little jewel when in Key West.

    Berlin's Cocktail Bar & Lounge - The freaking door that never stays closed. So much noise from the dining room

    Berlin's Cocktail Bar & Lounge

    (23 reviews)

    Cool, old school vibe with a view of the ocean. Great live music and enjoyed their dirty martini…read more Nice place to wait for our table

    Vibe is on point with being a speakeasy. The decor is dark and moody. The entertainment was…read morephenomenal. She sang and played percussion. Such a terrific voice and loads of talent. There is a small bar with about 12 stools, a small lounge area with about 4 small seating nooks, and then a high top bench area that is along the wall. Service and set up of this place is not conducive to being able to attend to patrons. Could only order food if you were seated at the bar. We sat at the high tops and you had to go to the bar to get your drinks. Problem is that the bar has patrons sitting as well so you are hovering over them waiting for a drink. It was very uncomfortable to impose upon others to try to get a drink. I am sure they didn't appreciate the audience as they were eating as well. The bartenders were way too busy and overwhelmed. Not only are they serving the seated patrons and the 4 small nooks, they are also making drinks for the attached restaurant. There were a gazillion tickets coming out of the printer and servers standing on the other side of the window waiting. It's just not possible to serve everyone with just two bartenders. We waited about 10 minutes for service. The drinks were underwhelming for a speakeasy. Just your typical menu. What we ordered was okay. They just missed a great opportunity to create unique twists on classics or to have craft cocktails. Even the classics (which are perfect for a speakeasy) weren't that great. For a speakeasy, the drinks are the main event. Glad we tried it as we always seek out speakeasies. Wouldn't go again.

    The Rum Bar - Inside the bar

    The Rum Bar

    (440 reviews)

    $$

    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.

    Pineapple Bar - cocktailbars - Updated May 2026

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