Best Bars and Venues in Key West for Live Music

Live music speaks to the soul and stirs something within, especially with a drink in hand! Key West's bars and pubs also serve as mini music halls, so great music can be found every night. Many classic, sticky-floor dive bars like the Hog's Breath and Sloppy Joe's feature sing-a-long rock and pop covers that everyone knows well enough to shout the refrain. Others showcase a wider range of musical genres, and you may uncover a new favorite band.

The newest addition to Duval Street is the Little Room Jazz Club, a sophisticated lounge that plays jazz and blues nightly, while the Smokin' Tuna is another rookie just off Duval Street with a large outdoor stage and all the hits. Head to Pete's Dueling Piano Bar for a musical battle followed by dancing late into the night, or take in some country tunes at Cowboy Bills before trying your luck with the mechanical bull.

With an eclectic musical line up, Green Parrot never disappoints, and the Rum Barrel's outdoor stage has attracted some big names - like Bo Bice from American Idol. For date night, Virgilio's serves up Italian fare and jazz music, while Schooner Wharf is a low key place to stumble into - or out of - down in the Historic Seaport.

Duval Street


You'd be hard-pressed to hear about Key West without hearing about the infamous Sloppy Joes bar, where people come to get – well – sloppy. It was one of Hemingway's favorite watering holes ("Sloppy Joe" was Captain Joe Russell, the founder...  Read More

Duval Street


Behind La Trattoria, Virgilio's – named after the founder of the restaurant – is an elegant spot for a cocktail. Single malt scotch, fine wines Perfectly mixed martinis are the house specialty - which are just $5 on Mondays. Every night...  Read More

Rum Barrel


Launched in 2006 by former Philadelphia 76ers President Pat Croce, the Rum Barrel offers a happening place to watch the game (particularly when Philly is playing) with plenty of spirits and great food to boot.There are over 150 rums and an...  Read More



Originally founded in Fort Walton Beach in the mid-70's, the Hog's Breath in Key West has been in business for almost 20 years. The bar motto is "Hog's breath is better than no breath at all" and this philosophy has been embraced by the regulars...  Read More



While many parts of Key West have seen modern changes, Schooner Wharf maintains that "old Key West" atmosphere - from the salvage wreckage decor, to the interesting characters that linger around the waterfront. It is also the home of the largest...  Read More



A true cowboy bar, the newly re-opened Cowboy Bill's Honky Tonk Saloon features line dancing, live country music performers, and - of course - a mechanical bull for watching wannabe cowboys try and show off. On select nights, they offer sexy...  Read More



Filled with mix of local characters and visitors-in-the-know, "The Parrot," is not your typical dive bar. As the oldest watering hole in Key West, they've got nothing to prove, and their motto, "No Snivelling," illustrates their no-nonsense...  Read More

Smokin' Tuna Saloon
Photo courtesy of Smokin' Tuna Saloon


Many of Duval Street's pubs are hole-in-the walls devoid of any natural light, but the Tuna is tucked away on Charles Street, leaving plenty of room for a sprawling outdoor area with a large performance stage and several outdoor tiki-style bars....  Read More



The Little Room Jazz Club & Wine Bar is a refreshing change amidst the Duval Street Troprock scene. Find a new favorite glass of wine from the extensive listing, as you listen to live jazz, blues and even Cuban-fusion bands. If you're...  Read More

Duval Street


At Irish Kevin's, hilarious entertainers (particularly Pauly from New York) persuade patrons from the street with a chant of "come on in!" The live performers have patrons dancing, singing and entering drinking contests. Music starts most...  Read More


Meet Amber Nolan

Originally from upstate New York, this restless traveler has a knack for befriending interesting characters. You can usually find her just about anywhere that has a hammock. Amber's favorite...  More About Amber