Duval Street Bar Crawl

Colorful Shops on Duval Street in Key West, Florida, USA
Colorful Shops on Duval Street in Key West, Florida, USA

In the city of Ernest Hemingway's retirement, the bar scene matters. Start from Mallory Square and make your way to Duval Street, stopping at these five places on the way:

1: Hog’s Breath Saloon, 400 Front Street

What to order: Rum Runner
Located closest to the water and Mallory Square, Hog’s Breath is as good a place as any to start your day. With a great selection of bar food, specialty cocktails and sweet merchandise, this bar pleases everyone. Make sure to have friends and family look you up on the Hog Cam while you’re there!

2. Sloppy Joe’s Bar, 201 Duval Street

What to order: Sloppy Rita or a microbrew
Welcome to Sloppy Joe’s, a Key West landmark and Hemingway’s go-to watering hole. Sit near the stage and enjoy some live music over drinks (they also have a great lunch menu). This is a good place to bring groups and an even better place to start your bar crawl down Duvall Street.


3. Rick’s Bar, 202 Duval Street

What to order: Strawberry daiquiri or something tropical
Known for their late night karaoke and live music that feels like its being played on a beach, Rick’s puts out the Key West vibes more than anywhere else. Only one of eight bars in this complex, a stop at Rick’s can either be a quick pass-through or an all-night event. 

4. Irish Kevin’s Bar, 211 Duval Street

What to order: craft beer or Green Alligator
Just when you’re wondering where to go next, a dozen voices from the bar next door will shout “COME ON IN!” Irish Kevin’s: It’s dark, it’s loud and you never know who’s going to be onstage when you go in – it could even be you if you stay long enough – but for anyone used to Irish pubs this place feels like home.

5. Fat Tuesday, 305 Duval Street

What to order: Famous frozen daiquiri
After a thirsty walk down Duvall Street Fat Tuesday is a sight for sore eyes. Here, daiquiris are the name of the game: pick one or two flavours to mix from the wall of swirling slushy machines and enjoy a refreshing drink and a break from the Florida heat.