Best Bars In Key West

Sloppy Joes
Sloppy Joes Bar And Grille
Photo:Steven Lamp

Where to begin?! Key West is known for its party atmosphere, so you can just guess at the number of bars down here. I have chosen ten very different bars that just about anyone could enjoy.

  • Sloppy Joe’s – Located on the corner of Duval and Greene Streets, this is the quintessential Key West Bar. Ernest Hemingway used to hang at the original bar long ago which just adds to the fame of this place. You can get a daiquiri or any other drink you like here along with some above average bar food. The also host several events and musical guests.
  • Hog’s Breath – The motto here is that Hog’s Breath is better than no breath at all. Well, I guess that point could be argued, but they do have some great entertainment here. Live music, and events such as 5K’s, fishing tournaments, and the homemade bikini contest all draw large crowds to 400 Front Street.
  • Green Parrot – Located on Whitehead Street, this bar has been names one of the best in the country by Playboy magazine. Probably because of the many eccentric people that tend to congregate here. On a normal day you may find some old hippies hanging out here along with some bikers, musicians, artists, fishermen, and tourists. This is also a major draw for musicians that perform here, year round and also during the Songwriters Festival.
  • Irish Kevin’s – When you are walking down Duval Street at night and you hear a bunch of yelling and music, it is probably coming from this place. There is usually someone on stage strumming a guitar, and they don’t miss a beat. As soon as someone does something funny in the crowd, they take note and yell it out to everyone in the bar. The customers here basically become part of the entertainment.
  • Berlin’s Cocktail and Cigar Bar – Located in the A&B Lobster House, this is an upscale bar where you can enjoy a drink before or after an amazing meal. The dark wood decor is definitely any man’s ideal idea of a bar. But even a girl like me can enjoy a martini or after dinner aperitif.
  • Captain Tony’s Saloon – This is the original building for the original Sloppy Joe’s where Ernest Hemingway actually did hang out. And you can actually check out he bar stool that Papa occupied. Back then, the bar was owned by Joe Russel. The building changed hands a few times until Tony Tarracino purchased the building in the late 1950’s and Captain Tony’s Saloon was born. Tony was a local celebrity: bar owner, captain, mayor, gambler, gunrunner, and actor. He died in 2008 at the age of 92 but the bar is a reminder of the this interesting man as well as the rich history of Key West.
  • Smokin’ Tuna – This bar is a hotbed for Key West’s musical talent. There is almost always some event or musical show being performed here. Check it out! And they have a raw bar to enjoy as well.
  • Virgilio’s – This martini bar and jazz club is one of the more sophisticated bars in Key West. Adjacent to La Trattoria, you can get a fabulous Italian dinner and enjoy a signature martini too.
  • Southernmost Beach Bar and Cafe – Located at the Southernmost Resort on the Beach, everyone wants to hang out at the beach with a frozen drink while vacationing on a tropical island, right? Well, this is the place to do it!

For more information about things to do and see in our island city, go to our Key West Web Site. You can also visit our Key West Events Calendar to see upcoming special events.

And for more restaurant reviews check out our restaurant review section of this blog as well as our restaurant reviews at

Island Genn – Your Key West Concierge