Party All Day and Night

Whether you're on a rum run or looking to prepare for today's sunset with a new flavor, Tipsy Rooster has what you need to keep the good times going. Be spoilt for choices as this contemporary bar and liquor store features a large selection of products distilled in Key West.

Have a drink at the bar and relax while enjoying the live local musicians performing. Tipsy Rooster serves some of the best specialty cocktails on the island featuring house-infused liquors.

As the slogan states, it's a 'Key West Tradition' to stop at Hemingway's favorite local bar who even gave it its name while he was living in Key West. Now the bar is one of the main attractions in town serving up food, cocktails and live music every day of the week.

The oldest bar in Florida, Captain Tony's Saloon was also the original location of Sloppy Joe's from 1933-1937. This bar gets its extra flair from bras hanging from the ceiling and business cards covering the walls.

Though you can find live music pretty much anywhere in Key West, the Green Parrot bar has been named one of the best live music venues in Florida. Bands from around the world perform onstage during Friday, Saturday and Sunday 5:30 to 7pm 'soundchecks' followed by a second late night performance.

'I came, I drank…I don't remember' is not only the slogan, but also likely a warning! Entertainers encourage audience participation in their performances at this fun Irish themed bar.

This world famous bar is a popular Key West watering hole complete with shop, restaurant and bar. Conveniently located at the corner of Front and Duval streets, they stand behind the fact that 'Hog's Breath is Better Than No Breath at All!'

A Key West classic, the Schooner Wharf is located in the Key West harbor providing patio seating and live band performances. They serve breakfast, lunch, dinner and late night snacks in this low-key bar on the water.

Spend the evening at this stylish cocktail bar offering an eclectic menu with delectable bar bites and a range of premium wines and beers. Have specially curated in-house cocktails while enjoying the lively ambiance and live music. 

This quaint wine bar has an extensive wine collection that is constantly changing to keep selections fresh and exciting. Enjoy a glass on the porch overlooking Duval Street or in its cozy, vintage setting.

Key West's largest entertainment complex features 8 bar venues, each offering a different experience from the rest. Options include a dance club, live music & sports bar, tree bar on Duval and more.

A world famous chain, Fat Tuesday's frozen daiquiris are guaranteed to cool you off after a long day on the town. This lively venue has a DJ every night and is one the hot dancing venues on Duval.

This downtown cabaret is only 3 blocks away from the Santa Maria Suites. La Te Da features an outdoor bar and restaurant as well as nightly performances from Christopher Peterson, Randy Roberts and more.

At this popular Key West bar & nightclub, 'Reality is a Drag' and drag is a reality! Nightly shows include performances from the Aquanettes with singing, dancing and comedy.