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While we do our best to ensure the accuracy of our listings, some venues may be currently temporarily closed without notice. Please confirm status on the venue website before making any plans.
Cocktail Bars
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After Work/Happy Hour
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Top Rated Nightlife in Key West

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Aqua Nightclub

Aqua Nightclub is one of the most popular nightlife haunts in the city. Known for its live music events, karaoke and other entertaining events; the club has amassed a large fan following. The place with its fun vibe, is known to be among the best for singles as well as LGBT, making it a convivial place to visit. If you are one of those people who love to tap their feet to dance numbers, Aqua Nightclub is your place to be. So when you are in the city and want to ring in the night with fun, frolic and laughter, head to Aqua Nightclub.

The Rum Bar at The Speakeasy Inn

Comfortably set inside the Speakeasy Inn The Rum Bar is a casual bar which serves a wide range of spirits in a laid-back atmosphere. The decor is rustic featuring a huge vintage-style bar, cushioned bar stools, wooden walls and a small TV mounted onto a corner of the bar. The place is particularly known for its specialty drinks such as the Rum Runner, Goombay Smash, Dark & Stormy and Hurricane. Also, try the Bahama Bomb if rum is your spirit of choice.

Little Room Jazz Club

Escape into oblivion with the smooth strains of jazz at the Little Room Jazz Club, an intimate cove for music lovers located on the dynamic Duval Street. This cozy haven features talented jazz musicians every night of the week, from the Hal Howland Trio and Ericson Holt, to the Denis Hyland Quartet and Terri White. Bring your date, sip on heavenly cocktails and let the night fold you into its embrace.

Blue Heaven

This much-loved restaurant reportedly was once the site of boxing matches refereed by none other than Ernest Hemingway. Now you will find avant-garde artwork in the gallery upstairs and great chow at modest prices in the restaurant. Caribbean flavors predominate and baking is done on the premises where desserts, rolls and breads pour from the ovens. All three meals are served here and Sunday brunch draws crowd. No reservations are taken, so be prepared to wait in line. That may, in fact, be half the fun.

Captain Tony's Saloon

Once a morgue and later an ice-house, this lively spot is one of the city's most popular bars and is said to have been the original Sloppy Joe's, entertaining author Ernest Hemingway. Jimmy Buffet sang here for a while in the beginning of his career and now live bands play nightly, who knows, perhaps you will hear the next Buffet. Stop by for a drink, or just to take a look at the "Hanging Tree," located inside the bar.


Virgilio's is one of the most widely visited cocktail bar, where cocktails and chilled martinis are not the only drinks served here. The bar possesses a penchant for letting you drink delicious wines and scotches, from all over the world, listening to soothing lounge music, accompanied by jazz and blues. The bar is never quiet because as the night comes closer, the volumes of the music go higher, making your evening an enjoyable one.

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