Nightlife in the Keys - Key West Style!

Key West has all kinds of bars, clubs, and theaters to satiate a nocturnal appetite. Nightlife starts early, just before the sun goes down, as everyone moseys down to Mallory Square and the two piers at the end of Duval Street or climbs aboard a vessel for a sunset cruise. Sounds of calypso and reggae fill the air as glasses clink in a toast to the setting sun.

Half an hour later, the crowd moves a few hundred yards to Front Street, where young night owls make their first stop at Hog’s Breath Saloon and jazz lovers take tables at Captain Hornblower’s. The rest proceed toward Duval Street for what’s locally known as the Duval Crawl.

If you’re one of those who loves bars Duval is truly Paradise found. There are more than enough watering holes along this one-mile stretch to keep you out—probably against your better judgment—until the sun rises.

Which ones match your taste? Just look at the clientele. It’s easy at establishments like the Bull & Whistle, which are either open-air or have indoor and outdoor bars with tables and atmosphere that spill out onto the sidewalk. Some, like Sloppy Joe’s, where Hemingway liked to gamble, are heaped in history. Others, like Jimmy Buffett’s Margaritaville Cafe and the 60’s-oriented Barefoot Bob’s, are themed. Those who can’t decide whether their favorite sport is copious quaffing, dancing, or football can have all three at Rick’s and Durty Harry’s, where several bars, dance clubs, live entertainment, and big screen TVs vie for your attention.

Want a bird’s-eye view of the action? Take the elevator to the Top, the seventh-floor lounge on the roof of the Holiday Inn La Concha Motor Inn, the island’s tallest building.

It’s an easy segue from Duval Street to Turtle Kraals in Land’s End Village, opposite the historic houses along Caroline Street, and the Key West Bight, where restaurants and bars like the Schooner Wharf Bar have turned the somewhat disreputable waterfront docks into one of Key West’s most characterful night spots.

Throughout the island the most popular places are glaringly tourist-oriented, but there are always enough resident characters who, as Jimmy Buffett sings, are "wasting away in Margaritaville," to add lots of local color.

Fanning out to Greene Street and Whitehead Street you’ll find bars of great character like Captain Tony’s Saloon, site of the original Sloppy Joe’s, and the Green Parrot, where you’re likely to find as many locals and Key West habitués as tourists.

The fashionable set need not feel left out for there are discreet piano bars like Flager’s at the Casa Marina and the Wine Galley in the Pier House, as well as art galleries that stay open until 10 p.m.

Many bars also have a good reputation for their solid refreshment. Don’t hesitate to order a conch salad, oysters, fish fingers, or sandwiches to accompany your libations.

Nocturnal wanderings aren’t limited to bars. You can dance yourself into a frenzy at the outrageously popular Epoch, a gay-oriented club that attracts everyone regardless of sexual orientation, and Havana Docks upstairs at the Pier House, where the crowd is more tennis tans and expensive smiles and the dance music is so good that even Yuppies work up a sweat. And over at the Poinciana, the only country bar in Key West, the music, dance, and dress are strictly western.

As well as its popular watering holes, Key West has live theater. (Some would say that Duval Street is live theater, but that’s another story.) The Red Barn Theater, for example performs dramas, comedies, and musicals, including works by Pulitzer Prize-winning and aspiring playwrights. The Key West Players present comedies and dramas at the Waterfront Playhouse, located in a former wrecker's warehouse. At the Tennessee Williams Fine Arts Center, the fare might be jazz, classical, or even a musical performed by national and international stars.

On a lighter note, while the Spirit Theatre recreates a spooky Victorian-era seance with super special effects, Théatre des Séances conjures up psychic thrills based on Key West’s history. And at the cabaret-style Club Chameleon they’re splitting their sides with laughter over hypnotists, musicals, and comedy reviews, followed by all-night dancing to grooved tunes.

For More Nightlife and Attractions, visit our Directory