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Nightlife

Before we get to more typical Key West nocturnal pursuits, why not consider taking advantage of the high quality offerings of local theaters, including Old Town's Red Barn Theater (319 Duval St.; 305/296-1520; www.redbarntheatre.com) for drama, comedy, and music performances and the Waterfront Playhouse (Mallory Sq.; 305/294-5015; www.waterfrontplayhouse.com) which claims to be the oldest continuously running theater group in Florida and puts on excellent stage performances, including some that will appeal to the kids. The Tennessee Williams Fine Arts Center (5901 College Rd.; 305/296-9911; www.tennesseewilliamstheatre.com) is on Stock Island and worth the 15-minute drive to catch concerts, plays, and performances by the Key West Symphony Orchestra and Key West Pops Orchestra.

For most Key West visitors though, drunkenness calls and drowns out the culture, and Duval Street is where most of the party palaces and inebriation stations are concentrated. Most are open to the street and awash in loud music – imagine a smaller-scale, tropical version of New Orleans' Bourbon Street and that's pretty much lower Duval. By all means, start with the most famous in town, Sloppy Joe's (201 Duval St.; 305/294-5717; www.sloppyjoes.com), made famous as a Hemingway hangout; the cavernous flag-bestrewn room offers up different music acts every night. One caveat: The Sloppy Joe's that Hemingway frequented (and immortalized as "Freddy's Bar" in To Have and To Have Not) isn't actually this one, but a smaller atmospheric joint around the corner now known as Captain Tony's Saloon (428 Greene St.; 305/294-1838; www.capttonyssaloon.com), where Jimmy Buffett got his start; owned since 1958 by Tony Tarracino, a colorful former gambler and mayor, the place is still an excellent pitstop for some local flavor, stuffed as it is with bric-a-brac and a tree growing through its ceiling. Newer watering holes that have achieved a certain notoriety, and following, include Margaritaville Café (500 Duval St.; 305/292-1435; http://margaritaville.com/cafe_KW.php), a touristy restaurant/bar opened by the abovementioned Parrothead-in-Chief and the grittier Hog's Breath Saloon (400 Front St.; 305/292-2032; www.hogsbreath.com), a 1988 offshoot of a Florida panhandle bar whose motto is "Hog's Breath is better than no breath at all." Hard to argue with that logic.

Gay nightlife is a key part of the scene in general, but a few particular spots clustered midway along Duval (around Angela and Petronia Streets) are standouts. The Bourbon Street Pub (724 Duval St.; 305/296-1992; www.bourbonstreetcomplex.com) is a hopping video bar with a small dance floor and quieter courtyard bar and pool. Across the street at 801 (801 Duval St.; 305-296-1992; www.801bourbon.com) you'll find a bar at street level, a popular drag cabaret upstairs, and a slightly more funky/naughty back bar. Newer additions down the street include a small gay men's stripper bar, Kwest (705 Duval St.; 305/292-8500; www.kwestmen.com) and a larger show/video/dance bar called Aqua (711 Duval St.; 305/294-0555; www.aquakeywest.com). Over toward the east side of the island, it's ladies only at Pearl's Patio (525 United St.; 305/292-2032; www.pearlspatio.com), part of Key West's only all-women's bar. The piano bar, low-key outdoor bar, and wonderful if slightly pricey drag cabaret at La Te Da (1125 Duval St.; 305/296-6706; www.lateda.com) is also quite entertaining. Practically de rigueur is the Sunday evening tea dance on the pier at the Atlantic Shores Resort (510 South St.; 305/296-2491; www.atlanticshoresresort.com), which is also a fun place to hang out by day – you can even sun yourself at its clothing-optional pool and quasi-beach.

See Key West Travel Guide