The bars on Duval Street offer everything from cheap dives to dueling pianos, and our itinerary includes it all! For those who wish to be able to maximize the amount of bars and minimize the amount of travel, we have compiled a Key West bar crawl that gives you a little of everything in a small amount of space.
Sleep in—you’re going to need it! When you finally rise from your comfy bed at The Inn at Key West, mosey down to our Tiki Bar by the pool and start your day with one of our drink specials! Gather your group by the largest pool in Key West and prepare for a day out on the town.
Hop out of the taxi at 124 Duval Street and start your engines with a shot at Smallest Bar. Like the name suggests, this bar is tiny! It’s too small to hang out inside, but it’s a great place to take a quick shot (and we mean alcohol and pictures).
Now that you've jump-started your day, head to 201 Duval Street. Sloppy Joe's has been a MUST in Key West since 1933 when the doors opened on the day Prohibition was repealed. A favorite "watering hole" of Hemmingway, the bar is known for its live entertainment, and is open 365 days a year. (Locals have been known to ride out hurricanes here.) Don't forget to grab a T-shirt with the world famous "Papa" picture and logo on it!
Next, head down the street to 305 Duval where you’ll find Fat Tuesday. This open-air bar is a great place to visit before the sun goes down! Their specialty is frozen drinks and they have ten different strong tropical flavors to choose from.
Now that you’re good and tipsy, walk two blocks up to 524 Duval and enjoy live music and tasty martinis at Virgilio’s! This dimly lit bar has an exposed ceiling from which you can view the sunset as you sip your drinks!
Another "legendary" Key West bar is located a few steps from Duval at 425 Greene Street. Captain Tony's saloon, is named for its owner and past mayor of Key West, Captain Tony Tarracino. This bar was a Jimmy Buffett favorite, and known patrons included Presidents Truman and Kennedy, Elizabeth Taylor, Truman Capote and Tennessee Williams. Try a "Papa Dobles"; a Hemminway favorite.
Before you go back down the bar scene, go up a bit further to 801 Duval and experience a different side of Key West nightlife! 801 Bourbon Bar is a dance club that features drag shows and cheap drinks! Keep your buzz going while watching or participating in one of the nightly shows.
After the show, make your way back to 224 Duval to the Bull and Whistle Bar. This three-story building has themed bars on each floor, and a little something for everyone. The drinks are strong, the dance floor is crowded, and the bartenders are friendly.
If you feel like singing, head next door to 218 Duval and check out Pete’s Dueling Piano Bar! The drink selection is fantastic, plus the piano’s play the best hits that have the entire bar singing along. It’s a great place to spend a few hours drinking and laughing with your friends.
If you feel like dancing, head a little further down to 202 Duval to Rick’s Bar where you’ll find live music downstairs and a DJ upstairs! The basement has live music, pizza, and strippers; the upstairs has a dance floor, and a DJ; both floors have cheap, stiff drinks.
Duval Street is full of Key West bars where good drinks and good times will be shared. Just make sure to take a cab back from your night out. Although it’s fun to party in Key West, always do so responsibly.