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Key West Nightlife

Aqua Nightclub
711 Duval Street
Key West , Florida
Tel: 305 294 0555

Just look for drag queens with bouffant hair, à la Sarah Palin, taking a cigarette break, and you've arrived at Aqua Nightclub, a hotbed of frivolous fun where female impersonator acts play out nightly. It's a typical Key West scene, with the crowd ranging from 30 to 70 years old, give or take a decade, and every shade of the sexual preference rainbow represented. The open ductwork ceilings sparkle with the prisms thrown about by the disco ball, and curtained booth areas line the back wall ($25 gets you Champagne service and a private nook here). There are two bars that host dueling bartender karaoke, and after the shows the dance floor gets going with everything from '80s throwbacks to classic dance tunes. There's no cover charge during the day, but the nightly shows cost $15 per person—unless you happen to be from Columbus, Ohio (as are the owners), in which case you'll get free entry.—Terry Ward

Open daily 2:30 pm to 2 am, nightly shows at 9 pm.

Bourbon St. Pub
724 Duval Street
Key West , Florida
Tel: 305 296 1992

Of all the gay bars on Duval Street, this is the most inclusive and is packed with as many locals as tourists. There's always a party going on here, with video screens, underwear-clad barkeeps, go-go dancers, and theme nights ranging from wigs to turbans to togas. Bourbon Street is part of a five-level complex that also includes a men-only guesthouse and the Garden Bar, a tiki torch–lit garden with a hot tub.

Bull & Whistle Bar
224 Duval Street
Key West , Florida
Tel: 305 296 4565

You wouldn't be caught dead at Duval Street's big-name watering holes (Sloppy Joe's, Margaritaville), but there's no shame in making your way to this long-standing come-as-you-are bar. The Bull & Whistle occupies a stately white building with delicate balconies that would look right at home on Bourbon Street. Likewise, drinking and live music are the main themes here. The ground level tends to be crowded with tourists and cruise ship escapees who get rowdy with sing-alongs (it's more mellow during the daytime). Upstairs, at the Whistle Bar, it's a more local scene, with two-for-one well drinks offered all day. People play darts and foosball under lazily spinning fans, to the strains of classic rock 'n' roll (think Crosby, Stills & Nash and Bruce Springsteen ballads). Angle for a stool on the second-floor balcony, which offers one of the best views over Duval Street. If it's your thing, head one level up to the rooftop Garden of Eden bar, a clothing-optional, open-air environment that is not for shy types.—Terry Ward

Open Mondays through Saturdays 10 am to 4 am and Sundays noon to 4 am.

The Green Parrot Bar
601 Whitehead Street
Key West , Florida
Tel: 305 294 6133

A few blocks removed from the Duval Street madness, the Green Parrot is arguably the most authentic watering hole on the island (the building dates from about 1890). Follow the absinthe-hued glow into the bar cooled by tropical breezes flowing through the screenless windows. And whatever you do, heed the "No Sniveling" mantra that hangs over the bar. It's a no-frills kind of place, with friendly bartenders; stiff drinks; and classic bar games like pinball, pool, and darts. The small stage hosts blues and rock bands on weekends; during the rest of the week, the jukebox pumps out classics from James Brown and B.B. King. The decor is a cozy hodgepodge—an open parachute over the bar, wooden parrots, a photo of Abe Lincoln, and random trophies stuffed onto shelving here and there. Your fellow bar mates are likely to be similarly diverse, from commercial lobstermen back from the catch to local dentists grabbing after-work drinks.—Terry Ward

Open Mondays through Saturdays 10 am to 4 am and Sundays 12 pm to 4 am.

915 Duval Street
Key West , Florida
Tel: 305 296 0669

If you're not into the college-kids-and-salty-locals scene, this sleek lounge is the perfect escape. Located above the restaurant Nine One Five, Point5 has an impressive amount of wines by the glass. They have a high-tech nitrogen system that keeps the wines fresh, if that's your sort of thing. If not, the DJs will keep you entertained. Even better, angle for a seat on the Victorian veranda to watch the nightly action on Duval Street below.

Open daily 6 to 11 pm.

Sloppy Joe's
201 Duval Street
Key West , Florida
Tel: 305 294 5717

This is one of those storied bars steeped in Key West history. Originally opened the day Prohibition ended in 1933 with the name Blind Pig, Sloppy Joe's moved to its current location in 1937. Papa drank here, of course, and legend has it Hemingway lobbied for the name change with a comment to then-owner Josie Russell, saying "Joe, you run a sloppy place—you should call this place Sloppy Joe's." The bar honors his memory, so to speak, with an annual Hemingway look-alike contest at the end of July. On any given day, the crowd is heavy on cruise ship day-trippers, but things perk up by sundown, when the tables are cleared for an impromptu dance floor and the live band rocks until 2 am. It's the best place to let loose with a sinfully sweet and strong piña colada.

The Top
Crowne Plaza Key West La Concha
430 Duval Street
Key West , Florida
Tel: 305 296 2991

Mallory Square may be the go-to destination for soaking up one of Key West's postcard-perfect sunsets. But when you're looking for a place to kick back with a drink in an atmosphere that's far less touristy—with iconic views all its own—head to this rooftop hotel bar. Push "T" in the Crowne Plaza's elevators to reach the unlabeled seventh floor (incidentally, the highest point in Key West), where the tiny bar occupies a breezy and unembellished outdoor space. Walk to the edge to view the length of Duval Street and watch the setting sun turn the rooftops of Key West's bungalows and church steeples a silvery pink. The bar always opens at 4 pm and closes "whenever the sunset watchers have wandered onward," quips a bartender.—Terry Ward

Opens daily at 4 pm.

Open daily 4 to 10 pm.

Information may have changed since the date of publication. Please confirm details with individual establishments before planning your trip.