Key West Bar Crawls

Find the best time to hit Duval Street and which bars to visit.

There are a lot of bars on Duval Street, and in Key West, so you need to know where to go before you get there. We can help - we have list the best bars in Key West!

While the sun’s still up…

Since you'd opted to start the day on Duval, head to Sloppy Joe’s at 201 Duval Street. This infamous Key West bar has been a must visit bar in Key West since 1933, when the doors opened on the day Prohibition was repealed. A favorite spot of Hemingway's, the bar is known for its live entertainment and for being open 365 days a year.

Next, head down the street to Fat Tuesday at 305 Duval. This open-air bar is a great place to visit any time. Grab a table in the courtyard and (at least) one of their notoriously strong frozen drinks, which come in ten different tropical flavors.

Now that you've got a buzz going, walk two blocks up to 524 Duval for a slightly more serious drinking. At Virgilio's, you'll enjoy live music and tasty martinis in a dimly lit bar offering sunset viewing as you sip your drink.

If you'd rather hit up anther legendary Key West bar, you can't go wrong heading off Duval to 425 Greene Street and Captain Tony’s Saloon. Named for its owner and past mayor of Key West Captain Tony Tarracino, this bar was a Jimmy Buffett favorite. Past patrons have included the likes of Presidents Truman and Kennedy, Elizabeth Taylor, Truman Capote and Tennessee Williams. Try a Papa Dobles, one of Hemingway's favorite drinks.

When the sun goes down…

Take a short breather from the bar scene and go up a bit further up Duval, to 801 Duval Street, to experience a different side of Key West nightlife. The 801 Bourbon Bar is a dance club that features drag shows and cheap drinks. Feel free to join the fun on stage, or just keep on drinking while you watch!

After the show, make your down to 224 Duval to the Bull and Whistle Bar. With themed bars on each of the three floors, there is sure to be something for everyone. The drinks are strong, the dance floor is crowded, and the bartenders are friendly.

If singing is more your thing, head next door to 218 Duval and check out Pete's Dueling Piano Bar. The piano's play hits that have the entire bar singing along while drinking from Pete's impressive drinks menu. It's a great place to spend a few hours drinking and laughing with your friends.

If you feel like dancing, head down to 202 Duval Street. At Rick's Bar, you'll find live music, pizza and strippers downstairs and a dance floor with a DJ upstairs; both floors have cheap, stiff drinks.

For more ideas on where to go in Key West, we have some nightlife suggestions.

After the bar…

Duval Street is full of Key West bars where good drinks and good times will be shared. Although it’s fun to party in Key West, always do so responsibly. If you're too far from Ocean Key Resort at 0 Duval Street to walk back, please take a taxi. If you started the night out in your car, be sure to tell the taxi driver that your car got drunk - they'll help you out and often will drive your car back to the hotel for you.