22 Best Nightlife in The Florida Keys, Florida

Although it's only open till 10, this is still a place to see and be seen. It's dark and a little mysterious, and the wine, wood-fired pizzas, cheese pairings, meats, and fondues are five-star worthy. Sit at the bar, on a couch, or at a high-top, and be transported to somewhere other than a typical, tropical Keys venue. The daily happy hour offers a "pizza and pitcher" special that's a hit with locals.

When it was the original Sloppy Joe's in the mid-1930s, Hemingway was a regular. Later, a young Jimmy Buffett sang here and made this watering hole famous in his song "Last Mango in Paris." Captain Tony was even voted mayor of Key West. Yes, this place is a beloved landmark. Stop in and take a look at the "hanging tree" that grows through the roof, listen to live music seven nights a week, and play some pool.

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.

There's history and good times at the successor to a famous 1937 speakeasy named for its founder, Captain Joe Russell. Decorated with Hemingway memorabilia and marine flags, the bar is full and noisy all the time. A Sloppy Joe's T-shirt is a de rigueur Key West souvenir, and the gift shop sells them like crazy. Grab a seat (if you can), and be entertained by the bands—and the parade of people in constant motion.

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.

Mingle with locals over cocktails and catch amazing sunsets from the comfort of an enclosed, air-conditioned bar. Floor-to-ceiling doors can be opened on cool days and closed on hot days.

Walls plastered with Bogart memorabilia remind customers that the classic 1948 Bogart-Bacall flick Key Largo has a connection with this watering hole. Although no food is served, and the floors are bare concrete, this landmark draws boaters, curious visitors, and local barflies to its humble barstools and pool tables. But the real magic is around back, where you can grab a seat on the deck and catch a postcard-perfect sunset. Live music draws revelers Thursday through Sunday.

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.

Come by boat or car to this oceanfront restaurant and sports bar, where you can soak in the views dockside or relax in the air-conditioning. Munch on fresh fish sandwiches or barbecue dishes while you shoot pool, catch the big game on large flat-screens, or dance to a live band or DJ. Late night can get a bit wild and loud.

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.

This open-air waterfront bar and grill retains its funky Key West charm and hosts live entertainment daily. Its margaritas rank among Key West's best, as does the bar itself, voted Best Local's Bar six years in a row. For great views, head up to the second floor and be sure to order up some fresh seafood and fritters and Dark and Stormy cocktails.

Marina views are among the many charms of this fun place in the heart of Key Largo. Sit outside under the tiki, in a brightly colored Adirondack chair by the firepits, or inside amid driftwood walls and prize catches. No matter: what you'll remember is the fresh, everything-made-in-house food.

A larger-than-life mermaid guides you to the kind of place you fantasize about during those long, cold winters up north. It's all about good drinks, tasty pub grub, and beautiful sunsets set to live bands playing island tunes and light rock nightly. Dining is all outdoors, on a deck or under the trees. Service is slow, sometimes even nonexistent.

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.

The area's glam celebrity hangout, Ziggie & Mad Dog's serves appetizers with its happy-hour drink specials. Its wine list and outrageous steaks have become legendary.