The Most Unique Bars in Key West (That Don’t Suck) in 2024

There are more than a few bars in Key West. There are so many that one would think drinking is Key West’s biggest attraction. It certainly is what some people go there to do, even the likes of Ernest Hemingway. For five years in the 1930s, Hemingway split his time hanging out with his 70 or so cats and tying one on at Sloppy Joe’s, his favorite watering hole. Since then, much has changed.

As I found with my 1st impression of Key West, the touristy main drag of Duval Street resembles a lot of what I don’t care for on Bourbon Street in New Orleans and the Vegas strip. You can find cheesy bars and chain restaurants in every tourist center in the world. But just as I found a better side of New Orleans and how I learned to love Las Vegas’s old-town charm, Key West has a plus side as well. With that in mind, here are 5 of the most unique bars in Key West that don’t suck.

Captain Tony’s Saloon

Contrary to the Hemingway memorabilia and T-shirts will have you believe, Sloppy Joe’s current location is not where Hemingway spent most of their time and, therefore, not on this 5 Unique Bars in Key West list. The original location, what is now Captain Tony’s, is just down the street. In 1938, one year before Hemingway left town, Sloppy Joe’s rent was raised, and instead of paying it, the bar relocated.

Besides being the actual spot where Hemingway used to drink, Captain Tony’s has a lot of character. It was once an icehouse, then a morgue, and is said to be haunted. Tick and tick for this unique Bars in Key West list. Inside, you’ll find barstools with the names of celebrities that behinds have once graced its presence. This includes John F. Kennedy, Truman Capote, and John Candy (I had to put a Canadian in there!) Oh, and myself, although I don’t think you’ll find my name there.

The Porch (Closed)

Note: The Porch has closed since this post was first published.

Although located in touristy Duval Street, The Porch is unlike the rest. Situated in a historic home, the Porch is one of the hippest unique bars in Key West as it is divided into two great bars – one serving craft beer and the other serving fine wine. This pairing, along with the Porch’s historic building, cozy deck seating, and large patio grounds, makes it a great spot to grab a drink in Key West.

La Te Da

In the heart of Key West’s vibrant nightlife scene lies the historic La Te Da Hotel, a multifaceted entertainment complex that seamlessly blends history and revelry. Once the dwelling and workshop of a local cigar manufacturer, the venue has transformed into an all-in-one destination with accommodations, a restaurant, multiple bars, and a vibrant outdoor patio. While the selection of beer, wine, and cocktails is noteworthy, its cabaret shows truly set La Te Da apart—an unmissable, adults-only journey into the island’s more risqué side.

The terrace and piano bar provide an excellent backdrop for an enjoyable evening, but the real allure lies in the captivating performances that offer a unique and unforgettable Key West experience. Be prepared to become part of the show, as La Te Da promises an evening filled with entertainment, history, and a dash of Key West’s inimitable charm.

Key West’s Smallest Bar

Another Duval Street find, the Smallest Bar in Key West, has big appeal. Sandwiched in an alley between two buildings, the Smallest Bar in Key West serves the biggest shots in town. It is the perfect place to grab a drink (or shot) while bar hopping or a place to meet some new friends. Unlike the crowded bars on Duval Street, its small size makes it easy to chat with the other patrons, making it one of the most unique and friendliest bars in Key West.

The Westin Drink Stand

Seeing the sunset from Key West’s Mallory Square is a must. Seeing the sun melt into the ocean while a“green thing” melts in your hand makes it that much better. Although technically not a bar, the Westin drink stand makes the most unique bars in Key West list for its long-term drink master. Jimmy, the bartender, has been serving up this signature cocktail from the Westin’s waterfront patio for over a decade.

I can’t recall exactly what went in it, but I can say that it is super tasty, and Jimmy will gladly let you know the ingredients while serving it up to you. They are a hefty $10 but are large in size and taste, so they are worth the price.

The Green Parrot

The Green Parrot has been serving booze in Key West since 1890. This popular local bar could be listed by SNL’s Stefon as one of the hottest spots in town. It is an equal parts dive bar, local hangout, great music venue, and possible stabbing location – if you are into that sort of thing. Jokes, of course.

As the “first and last bar on US1” highway, the Green Parrot is definitely one of the most unique Bars in Key West.

Take a Cocktail Tour of the Most Unique Bars in Key West!

Exploring Key West’s unique bars is an authentic island experience that pairs better with friends. A cocktail tour unveils this vibrant destination’s history and culture through its diverse drinking establishments. These bars, each with a distinct personality, share tales of Key West’s past and present. From historic gems to modern hotspots, the most unique bars in Key West offer more than just drinks – they provide a glimpse into the island’s soul.

Joining a cocktail tour is a journey into mixology and storytelling. It ensures you savor the essence of Key West in every sip. I recommend this Key West Cocktail tour for a fun night out!

Alternatively, if you are into Jimmy Buffett, there’s a fantastic tour that covers this locally loved musician’s life in Key West.

Need to Sleep it off These Unique Bars in Key West?

I stayed at the uniquely awesome NYAH hotel to recover from Key West’s nightlife. It offers the best combination of value and comfort and is within walking (or stumbling) distance from all the bars listed above. I highly recommend it!

For an authentic taste of Florida, opt for a getaway at the Margaritaville Key West Resort & Marina, nestled near Mallory Square. Revel in the scenic vistas from your balcony, relish deck-side dining, and unwind with a rejuvenating massage at this renowned luxury resort.

Alternatively, the DoubleTree by Hilton Hotel Grand Key Resort – Key West offers a delightful experience with its zero-entry pool, refreshing tropical beverages at the Tiki Bar, and a tempting dining option at the Palm Haven Restaurant. Plus, its convenient proximity to the airport ensures guests can seamlessly transition into a lap of luxury upon their arrival in Key West.

Drink Up at the Most Unique Bars in Key West

Key West’s vibrant and diverse bar scene offers a unique and memorable experience for every type of traveler. Each bar contributes to the colorful tapestry of Key West’s nightlife, from historic haunts with intriguing stories to quirky spots boasting unconventional themes. Whether you find yourself sipping cocktails at an iconic speakeasy or enjoying live music at a waterfront venue, the island’s bars are more than just places to grab a drink – they are reflections of Key West’s rich history, eclectic culture, and unwavering spirit.

So, the next time you find yourself in this tropical paradise, embark on a bar-hopping adventure and discover the unparalleled charm that sets Key West’s drinking establishments apart. Cheers to a journey filled with unique libations and unforgettable moments!

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For more reviews from Key West and beyond, see HERE.