Top Bars in Key West – It’s 5 0’clock Somewhere

Top Duval Street Bars in Key West

The top bars in Key West are hard to pick because Key West has so many great bars.  Our bars compare to no other place. All due respect to any other party city in the USA, Key West is the best party town…no competition…well maybe New Orleans, but, they come in as a distant second. The big difference between the two party cities is that Key West is safe and clean. The weather is perpetually sunny year around, the people on the street and bars are extremely friendly, the drinks are very generous and you can get then inexpensively during Happy hour. Key West is everything you expect from your tropical vacation and so much more!

Key West… It’s 5 O’clock Somewhere!     
Key West Duval Street Bars
Although some people try, you can’t possibly drink in all of Key West’s bars in one night or even two. There are just too many great places to choose from. My picks for the best Duval Street bars in Key West include: 

Sloppy Joe’s

Sloppy Joe’s, founded in 1933 and in its current location since 1937, was a one-time hangout for Hemingway and is still one of the most popular and entertaining bars in Key West. Sloppy Joes is always busy. Even on a Monday night in the off-season, and the large stage attracts the best bands playing in Old Town– the music and dancing keeps you going until 2 a.m. Be sure to make all of your friend’s jealous of your Key West trip by saying hi on their famous webcam. 

The Hog’s Breath Saloon

Although Hog’s Breath Saloon is partly hidden right off of Duval Street, it still has maintains the feel of a true biker bar despite its obvious appeal to the Key West also has to its tourist trade.  In typical Key West tradition, live bands, up and coming songwriters, talented local bands and musicians dominate the entertainment calendar, and it’s almost required that visitors leave wearing a Hog’s Breath t-shirt emblazoned with the saloon’s famous motto: “Hog’s Breath is Better than No Breath at All.” Here, too, you can taunt your friends by saying hi on the webcams too. 

The Bull and Whistle

The Bull and Whistle is really three fun bars all wrapped up in one…don’t forget to go to the top for the famous Garden of Eden – also some of the best DJ’s on the island play great dance music…naked or dressed! The ground-level Bull is dominated by a large central bar with a small performance stage in the corner with talented local musicians, while the second-floor Whistle is more of a sports bar with a pool table, darts, an amazing narrow second-floor balcony to drink and…and of course, people watch. 

Top Duval Street Bars in Key West


Captain Tony‘s

This is the site of the original Sloppy Joe’s — which moved across the street in a spat over rent many, many years ago. Although, this is right off of Duval Street, we had to include it…because it’s famous and fun and well…you just need to stop in and see for yourself. Then, place your business card on the wall for future visits to reminisce. Captain Tony’s was Hemingway’s Key West hangout for many years and retains a wealth of local history, much of it hanging from the walls of the bar and that it used to be a morgue. That tree you might be leaning against with your drink, for example, was Key West’s ‘hanging tree’ in the 19th Century, so your companions could include the ghosts of some pirates who had their necks stretched by local vigilantes. Located on Greene Street, Captain Tony’s has live music nightly.

The Smallest Bar

Like the name implies, this is the smallest bar in Key West. I’m not sure what the fire code says about maximum occupancy, but it can’t be more than about 10…but it’s been said to have as many as 22 crowded in. People try to break the record. Stop in and find out what the current record is. There are only about three barstools, but it’s a great place to take over with a (small) group of friends, and there’s plenty of interaction with curious passers-by on Duval Street.
There are many more great bars on the island, such as The Conch Republic Seafood’s bar, 2 Cent bar, Vino Wine Bar, Cowboy Bills, and more. As mentioned, may not be able to drink at every bar in key west, but you can have fun trying! You may as well eat drink and be merry, for tomorrow you may … do it all over again!
by Marjorie Spoto
Destination: Key West, Florida