5 Unique Bars in Key West that Don’t Suck


There are more than a few bars in Key West. So many so that one would think drinking is Key West’s biggest attraction. It certainly is what 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 favourite 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. Cheesy bars and chain restaurants you can find in every tourist centre 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 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 this 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 up and left.

unique bars in Key West

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 (had to through a Canadian in there!) Oh and myself although I don’t think you’ll find my name there.

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The Porch

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, cosy deck seating, and large patio grounds makes it a great spot to grab a drink in Key West.

unique bars in Key West

Key West 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 is easy to chat up the other patrons making it not only one of the most unique bars in Key West, but the friendliest as well.

unique 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 this unique Bars in Key West list for its long-term drink-master. For over a decade, Jimmy the bartender has been serving up this signature cocktail from the Westin’s waterfront patio. 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 hefty $10 but are large in size and taste so worth the price.

unique bars in Key West

unique bars in Key West

The Green Parrot

Known as the first and last bar on US Highway 1, 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. Equal parts dive bar, local hangout, great music venue, and possible stabbing location – if you are into that sort of thing. Jokes of course. The Green Parrot is defiantly one of the best unique Bars in Key West that don’t Suck and not to be missed!

unique bars in Key West

unique bars in Key West

Need to Sleep it off?


    Find the best deal, compare prices, and read what other travellers have to say about NYAH at TripAdvisor

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



What say you?
Know some Unique Bars in Key West not listed here?
Let’s hear it!

For more reviews from Key West and beyond see HERE.

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11 replies on “5 Unique Bars in Key West that Don’t Suck”
  1. Avatarsays: Jessica

    Captain Tony’s is the best! Although I’m a bit of a sucker for anything that’s pirate/sailor themed so I might be biased.

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  4. Avatarsays: Scott Petak

    Jimmy at the Westin has been there since the hotel opened in 1996… he is an icon in KW and the best damn bartender on the island. I had te privalige of working with him for 8 years… he is the BEST.

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