Key West Entertainment

  1. Aqua

    For a peppy scene that includes dancing and occasional drag shows, men and women should head to Aqua.

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  2. Bourbon St Pub & 801 Bourbon Bar

    Gay nightlife, in many cases, blends into mainstream nightlife, with everybody kind of going everywhere these days. But the backbone of the gay bar scene can be found in a pair of cruisey-type watering holes that sit across the street from one another, Bourbon St Pub and 801 Bourbon Bar (801 Duval St), which can be summed up in five words: drag queen-led karaoke night.

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  3. Captain Tony's Saloon

    The propagandists would have you believe Sloppy Joe's was Hemingway's original bar, and that's technically true, but the physical place where the old man drank was right here (Sloppy Joe's was eventually moved around the corner and into frat boy hell). Hemingway's third wife (a journalist sent to profile Poppa) seduced him in this very bar, wallpapered with business cards from around the world (including this travel writer's).

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  4. Cowboy Bills

    Do your best bow-legged saunter here for some (very) over-the-top country-n-western vibe, live honky tonk and weekly 'sexy bull-riding' competitions. If you just spilled your Miller High Life in excitement, turn off Blue Collar Comedy Tour and git on down here.

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  5. Garden of Eden

    Go to the top of this building and discover Key West's own clothing-optional drinking patio. Lest you get too excited, cameras aren't allowed, most people come clothed, and those who do elect to flaunt their birthday suits are often…erm…older.

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  6. Island Dogs Bar

    'Come as you are,' reads the sign, and as it's written, so it goes in this hip (for Key West) joint, which seems to attract a younger crowd.

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  7. Pearl's Rainbow

    Gay women will enjoy the backyard pool bar at the women's inn, Pearl's Rainbow.

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  8. Schooner Wharf

    Schooner Wharf manages to work in three happy hours a day.

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