12 Best Nightlife in Key West, The Florida Keys

Pause for a libation in the open air and breathe in the spirit of Key West. Built in 1890 as a grocery store, this property has been many things to many people over the years. It's touted as the oldest bar in Key West, and the sometimes rowdy saloon has locals outnumbering out-of-towners, especially on nights when bands play.

Key West's largest gay bar, Aqua hosts karaoke contests, dancing, and live entertainment at three bars, including one outside on the patio. For an evening like no other, come see the Aquanettes at their "Reality Is a Drag" show.

Pick your entertainment at the Bourbon Street Complex, a club within an all-male guesthouse. There are 10 video screens along with dancers grooving to the latest music spun by DJs at the Bourbon Street Pub.

This megasize entertainment complex is home to eight different bars and clubs, both indoor and outdoor. Their motto is "Eight Famous Bars, One Awesome Night," and they're right. You'll find pizza, dancing, live music, Rick's Key West, and the infamous Red Garter strip club.

Perhaps one of Duval's more unusual and intriguing watering holes, the Garden of Eden sits atop the Bull & Whistle saloon and has a clothing-optional policy. Most drinkers are lookie-loos, but some actually bare it all, including the barmaids.

Belly up to the bar for a cold mug of the signature Hog's Breath Lager at this infamous joint, a must-stop on the Key West bar crawl. Live bands play daily 1 pm–2 am (except when the game's on TV). You never know who'll stop by and perhaps even jump on stage for an impromptu concert (can you say Kenny Chesney?).

Part of a men's resort, Island House Bar & Café serves frozen and other cocktails along with creative cuisine in tropical gardens with a pool where clothing is optional. It is open 24 hours.

This venue hosts female impersonators (catch Christopher Peterson when he's on stage) and riotously funny cabaret shows nightly in the Crystal Room Cabaret Lounge. There is also live entertainment nightly, featuring a variety of local stars, including the ever-popular Debra in the ultracool Piano Bar.

A youngish, touristy crowd mixes with aging Parrot Heads. It's owned by former Key West resident and recording star Jimmy Buffett, who has been known to perform here. The drink of choice is, of course, a margarita, made with Jimmy's own brand of Margaritaville tequila. There's live music nightly, as well as lunch and dinner.

The party begins at the Beach Bar, with live entertainment daily to celebrate sunset on the beach, and then moves to the Chart Room. It's small and odd, but there are free hot dogs and peanuts, and its history is intriguing.

Love karaoke? Get it out of your system at Two Friends Patio Lounge, where your performance gets a live Internet feed via the bar's Karaoke Cam. The singing starts at 8:30 most nights. The Bloody Marys are famous.