Best Bars in Key West

Having played host to renowned personalities like Tennessee Williams and Jimmy Buffet, the Chart Room Bar hardly needs an introduction. Located within the luxurious Pier House Resort and Caribbean Spa, Chart Room has a very cozy and comfortable atmosphere and therefore, has been a favorite of the city locals for several years now. It is a great place to hang out with friends and indulge in some private conversation over a couple of drinks. Once inside, you will forget that you're within one of Key West's most luxurious resorts, as the bar has a very modest yet pleasant feel to it.

The Waterfront Brewery is one of the biggest breweries in Key West serving customers a wide range of beer such as their signature Crazy Lady, Truman Double IPA and Pallina, that have been brewed on-site. The brewery also has an extensive menu featuring appetizers, salads, soups, handmade sandwiches, entrees, and dessert. The Waterfront Cuban sandwich, Nut Crusted Mahi-Mahi, and the Bahamian White Conch Chowder are some of the must-tries from the menu. The brewery also offer tours around the facility for people who wish to know more about their brewing processes.

Wild groups gather at this open-air bar nightly, to party 'til they drop. If you are up for a pretty rambunctious scene, you will enjoy this antique saloon built in 1890 and generally agreed upon as the oldest bar in Key West. The co-owned smokehouse next door called "Meteor," serves pork, chicken, beef and seafood until 2am. Play pool, darts, or pinball while trying a "spine-tingling" cocktail. On weekends, there is live music, and the jukebox pounds out blues, zydeco and reggae all week. Don't miss this spot, listed as one of the "World's 50 Greatest Bars."

Founded in 1933 on the day Prohibition was repealed, this famous bar became one of author Ernest Hemingway's favorite drinking spots. In fact, it is rumored that Hemingway even came up with the name "Sloppy Joe's." Nowadays, the bar has a very casual atmosphere, hosts live bands, and serves good meals, including the original Sloppy Joe sandwich. With live entertainment and a lively crowd, this is one of the best parties in town. It is also the home of a Hemingway look-alike contest.

In the late 1930s, famed author Ernest Hemingway lounged in the seats of this now famous bar. Formerly rooted in Duval Street, Captain Tony’s Saloon is today housed in a building on Greene Street. However, more than the history associated with it, the eerie ambiance of the restaurant is what attracts droves of curious tourists to this spot. Upon entering, a large tree captures diners’ attention. The ominous tree is fabled to have been used to hang criminals. Additionally, gravestones spread across the dining area add to the macabre vibe of the establishment.

You're sure to be spoiled with the entertainment options available at Schooner's Bar. Drink, dine, dance, cheer, or shop...till you drop! With happy hours from 8a-noon, you're sure to have a great start to your day. The vast menu offers items, such as Fresh Stone Crab Claws, Conch Chowder and Fresh-Shucked Oysters. Don't worry - you can burn those calories up dancing the night and day away! Cheer for your favorite team at the Minimal Regatta, Schooner Wharf Wreckers Race, Barbecue Cook-off, Chili Cook-off, or the king of all Key West events, the Battle of the Bars. You can even plan a party on Key West's flagship, The Schooner Western Union, which docks here. With such fine entertainment offerings, it's no surprise that the bar has been highly acclaimed by Aqua Magazine as well as the New York Times.

Rick's Bar is one of the most popular nightlife haunts in the city. People love visiting this trendy club due to its mind blowing DJ, karaoke and live music events. The place has a vibrant and contagious vibe, with a friendly and efficient staff; coupled with an impressive list of alcoholic drinks. The bar is mostly frequented by a cheerful crowd of youngsters who bring in dance and excitement to the pub. Rick's Bar invites you to bring your friends along to an evening well spent.

At Hog's Breath, the motto is "better than no breath at all," and who can argue with that simple logic. You can even buy hats and shirts with that adroit slogan. While the restaurant and raw bar are a draw, they are not the main lure here—the sunset view is. Hog's Breath is right across the street from the Mallory Dock sunset festivities. Live entertainment goes on daily, as does the partying. Try Hog's Breath beer, raw oysters and a fish nugget sandwich with tartar sauce.