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Best Key West Nightlife

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Key West is a place for fishermen, divers, treasure hunters, artists, writers, the lost, the lonely and those who just don’t belong anywhere else. But first and foremost, it’s a party town. People come here to fish, dive, sightsee, dine and shop, but those are just pursuits to fill the time between cocktail hours. Finding suitable establishments to enjoy a crowd and a cocktail requires very few motor skills, seeing as how one is often separated from the next by a mere sheet of drywall. The famed “Duval Crawl” acknowledges the proliferation of saloons along the main street. Key West’s reputation as a serious drinking town wasn’t hurt by Hemingway’s notorious presence, and one can only imagine the vast lakes of alcohol consumed on this flyspeck of coral rock before and since Papa left town. A bottle of Jack is a bottle of Jack anywhere, so choices boil down to ambience, price and entertainment. The only problem is that when someone says “bottoms up” in Key West, you’re never quite sure if all they’re proposing is a toast. The city’s boisterous and thoroughly unabashed GLBT community has gone mainstream, with transvestite show clubs being among the more popular entertainment options.

801 Bourbon Bar and Cabaret

Neighborhood: Old Town
If you’ve never watched a burlesque show starring female impersonators, this is the time. At 801 you’re going to be assaulted by lip-synching, outrageous behavior and plenty of cleavage ... on these guys. You can even play Drag Queen Bingo on Sunday afternoons if you’re really open-minded. It’s all in good fun and there’s no need to cover your face when walking in or out the door, this is Key West and nobody gives a damn. Most afternoons, the “girls” will be out on the sidewalk in their chiffon dresses rounding up customers before show time.

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Bull and The Whistle

Neighborhood: Old Town
The loud music from within the Bull and The Whistle, a conspicuous white building with open windows, wafts over the sidewalks for a block in either direction. Many stop to watch, some walk in, most move on. But those who do enter will find something completely different from Key West’s other bars. The first floor is dark, but if you poke your head in during the day you’ll see colorful murals depicting old Key West scenes. The second floor bar is cool and a nice prep area, where you can toss down a couple of cold ones before making your move up to the rooftop Garden of Eden, which is full-on clothing optional. Luckily there’s no dart board.

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Captain Tony's Saloon

Neighborhood: Old Town
In the location of the original Sloppy Joe’s, this dingy joint was owned for about 30 years by Captain Tony Tarracino. A charter boat captain, former mayor and local celebrity, Captain Tony was as salty as Key West itself. The bar reflects the memory of his earthiness with the ceiling, pilings and walls covered with license plates, business cards and ladies’ panties. A thick tree erupts from the floorboards and goes through an opening in the roof. Tony often greeted repeat customers with a handshake and the comment, “I’m truly sorry if I stepped on your face last night.” You’ll usually encounter a jovial and feel-good crowd on hand (or on the floor) here.

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Bourbon Street Pub Complex

Neighborhood: Old Town
I don’t know if there’s a Duval Street bar in New Orleans, but you sure won’t forget this Bourbon Street experience in Key West. Located in the GLBT section of Duval Street, it’s a gay-friendly pub on the first floor and clothing-optional on the upper level. Straights are welcome, too, as it’s a big ol’ party worthy of the Quarter, pre-Katrina.

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Bourbon Street Pub Complex  

Rick’s and Durty Harry’s

Neighborhood: Old Town
This raucous complex of bars in the heart of the Duval Street saloon corridor offers a variety of settings. There’s an upstairs bar, downstairs bar, sports bar, outdoor “Tree” bar and a hip-hop dance club with a DJ. Hard rock and heavy metal are the themes at Durty Harry’s. The place really smokes during spring break with wet T-shirt contests and other entertainment for the young at heart.

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Rick’s and Durty Harry’s  

Green Parrot Bar

Neighborhood: Old Town
It’s not easy to find this bar near the Truman Annex, but it’s worth the trouble and provides a respite from the din of Duval Street. The Green Parrot has been a popular meet-up watering hole since 1890 and offers pool, pinball and darts. The slightly clandestine location means you’ll usually find more residents than visitors on hand, and that means prices on food and drinks are more reasonable than in the visitors-only pubs.

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Irish Kevin's

Neighborhood: Old Town
This is our favorite watering hole in Key West, though the fact that we’re Kellys probably puts our objectivity in question. Irish Kevin’s is jammed most nights with visitors and locals. A bar counter runs down most of one side of the place, with prompt table service to boot. Entertainers strum the guitar, sing and interact with the audience. The humor is mostly off-color, so if that offends you, try another bar, like one in Cleveland.

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Hog's Breath Saloon

Neighborhood: Old Town
The mantra here is “Hog's Breath is better than no breath at all.” If you’ve ever spent time on a farm you may not agree, but this party palace was the brainchild of an Alabamian, well, what more can we say? The bar has been breathing since 1988 and has hosted a lot of misspent hours and music, including headliners like Kenny Chesney, in the 20-odd years since. There’s a full calendar of special events, from fishing tournaments to the homemade bikini contest held each year during Fantasy Fest. The raw bar and a grill will stifle hunger pangs and there’s even a party room used for social gatherings and ... weddings? Yep, as in “We had our reception at the Hog’s Breath Saloon.”

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Sloppy Joe's

Neighborhood: Old Town
Lawsuits have been filed over the trademark of Sloppy Joe’s, who owns it, where is the original? Sloppy Joe Russell was a fishing and drinking pal of Hemingway’s back in the 1930s, and the bar that now carries his name remains open 365 days a year to celebrate the art of pouring alcohol down your gullet. It’s loud and it’s crowded, sometimes so much so that it’s too much trouble elbowing your way in. Bands do their thing until the late hours, and remember, no matter how much fun table dancing looks, don’t try it after more than one drink.

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