As perfect as a day on Key West's gorgeous beaches may sound, we promise that the island holds even more once the sun goes down. Sip whiskey in a bar Ernest Hemingway used to haunt or down a Jimmy Buffett-approved pitcher of margaritas at one of the many oceanside shanties.

Music, often live, pours out of the bars along Key West's main strip, inviting you in for more than just a round of shots. The Green Parrot Bar (601 Whitehead St., Key West, 305-294-6133; www.greenparrot.com) is a favorite of locals and visitors alike, lending the true Key West experience for its patrons at the beginning of the night for a bite or after midnight for a swirl around the often-packed dance floor. The Green Parrot has live bands each week and a world famous jukebox to keep you shaking it late into the night. There are other beloved standbys to hit up like Sloppy Joe's Bar (201 Duval St., Key West, 305-294-5717; www.sloppyjoes.com) and Captain Tony's Saloon (428 Greene St., Key West, 305-294-1838; www.capttonyssaloon.com), but for drag and dancing, it's all about Aqua Nightclub (711 Duval St., Key West, 305-294-0555; www.aquakeywest.com). Key West's most fabulous show, "Reality is a Drag," is on the stage every day at 9 p.m. and the (no cover!) Weekend Dance Party happens Friday and Saturday at 11:30 p.m. Aqua is open until 2 a.m. or later (depending on the crowd), so if you end up there late night, you might as well plan to enjoy the beautiful Key West sunrise.

Need a little guidance in your Key West nightlife planning? At sundown each day, local artisans, street performers, food vendors and even psychics gather at Mallory Square to enjoy the sunset and kick off the nightly party. Get your group together and do a Key West Pub Crawl that spans five different bars—including a drink at each bar—all for only $30. If you'd rather turn your boozing into a friendly game, one that does not involve a deck of cards or a funnel, join in a "Best of the Bars" Southernmost Scavenger Hunt (www.keywesthunt.com). Get your drink on as you travel around to local favorites and well-known spots. You never know where you'll end up—and chances are you might even catch another stellar Key West sunrise.

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