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Don's Place is a popular bar in Key West known for its casual and laid-back vibe, making its guests feel at ease from the get go. The interiors are cozy yet lively with hardwood floors, well-spaced seating areas, a foosball table, a ping pong table, a jukebox and four wall mounted LCD screen TVs. The bar has everything you need, from craft beers and to a notable selection of local spirits and wines. You can also purchase bottled beers and wine from their on-site liquor store.
One of Key West's premier LGBT bars, Bobby's Monkey Bar is where a large chunk of the city's gay come to socialize and have a good time. The interiors are exactly what you expect from a dive bar; minimalistic decor, dim lighting, and basic seating arrangements. The bartenders are friendly and offer you drinks that match your taste. The bar hosts karaoke and pool competitions on Sunday nights, when the bar tends to get a bit crowded.
Located in the Old Town of Key West, this restaurant has a unique menu that combines seafood as well as steaks. The choice is extensive just like their portions, so you are in for a feast. Don't forget to try the Lime Shrimp and the fresh catch of the day that is served with Caribbean salsa, rice and grilled vegetables. The bar is a great place to unwind. An amazing and appetizing experience for your taste buds is guaranteed out here.
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Founded in 1933 on the day Prohibition was repealed, this famous bar became one of author Ernest Hemingway's favorite drinking spots.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.
Once a morgue and later an ice-house, this lively spot is one of the city's most popular bars and is said to have been the original Sloppy Joe's, entertaining author Ernest Hemingway. Jimmy Buffet sang here for a while in the beginning of his career and now live bands play nightly, who knows, perhaps you will hear the next Buffet. Stop by for a drink, or just to take a look at the "Hanging Tree," located inside the bar.
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.
Unless you live in Key West, you will only find the Hogfish Bar and Grill on a tip. It’s off the beaten track and a little tricky to find, but it is well worth the search. Once there, you know instantly this is a local’s spot. The Hogfish Bar and Grill is the way the Keys used to be. Right on the waterfront, it’s a place to savor the pleasure of peeling and eating fresh Key West Pink Shrimp, while watching shrimp boats dock. It’s as if nothing has changed in 50 years. Dig into a fresh Hogfish sandwich and enjoy the live music.