4 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.