Photo credit: Marina K. Villatoro /Gringa TravelingMom

Photo credit: Marina K. Villatoro /Gringa TravelingMom

During my search for places to visit on Key West I learned a lot about the place, I also found the region’s most legendary and traditional bars of all – Sloppy Joe’s.

I contacted them to see if it was possible to make a reservation. They recommended that it was best to go for lunch if I was bringing kids. It turns into a live music nightclub with food at night.

But in this case, after a long time, I was able to say that it would be an adult night out. We were on a mini honeymoon and we wanted to enjoy live music and drinks.


Sloppy Joe’s is located on the fun side of Duval Street. This is where all of the main action takes place. There are bars, restaurants and tons of foot movement on the streets.

We arrived at 6 pm and the restaurant was already packed! This surprised and excited me at the same time, I mean, if it was this full, it had to be good!

Photo credit: Marina K. Villatoro /Gringa TravelingMom

Photo credit: Marina K. Villatoro /Gringa TravelingMom

At the entrance it says to seat yourselves but I had to ask for some help. There was so much commotion! Luckily a staff member showed us to a table right in front of the stage. That night there was a live music act by Pete and Wayne. They have been performing here for almost twenty years.

I don’t get out much and this felt like so much fun! Their skits and songs were brilliant and even a bit racy. Sloppy Joe’s was exactly what I needed.

How To Enjoy Sloppy Joe’s Key West

This is not just a place to eat and run. So plan on spending a few hours here. Whenever a fun act is on, you will want to stay all night. No one ever pushes you to leave or vacate your table.

They offer the famous Sloppy Joe sandwiches, which Ernest Hemingway recommended naming the place after. However this isn’t a place you visit for the food, you come here for the food, plenty of drinks and the fun atmosphere.

History of Sloppy Joe and Key West

    • The official opening of Sloppy Joe’s Bar was December 5, 1933–the day Prohibition was repealed. But it opened long before.
    • The bar went through two name changes and a sudden change of location before it became Sloppy Joe’s.
    • Its first name was Joe Russell, after its owner, but later became the Silver Slipper when a dance floor was added. But the name wasn’t accepted by costumers.
Photo credit: Marina K. Villatoro /Gringa TravelingMom

Photo credit: Marina K. Villatoro /Gringa TravelingMom

  • Hemingway who was a favorite patron of Russell’s bar from the start encouraged its name change to Sloppy Joe’s.
  • Sloppy Joe’s migrated across the street to its present location on May 5, 1937.
  • In true Key West fashion, the bar never actually closed during the transition. In fact customers picked up their drinks and carried them, along with every piece of furniture in the place, down the block.
  • The new Sloppy Joe’s boasted the longest bar in town.
  • When Hemingway left Key West in 1939, a few of personal effects were stored in a house next to Sloppy Joe’s.
  • After the house was sold, the effects were moved into the back room behind the bar at Sloppy’s.
  • Joe Russell died in 1941 of a heart attack. He was 53 years old.
  • Hemingway’s stuff remained behind the bar until 1962, a year after Hemingway’s death.
  • His widow opened the room and took possession of them. Some of the memorabilia was given to the then-owner of the bar to be displayed.
  • Hospitality remained the same over the years. Now, Sloppy Joe’s has three complementary divisions: food, beverage, and retail store.
  • Over the years Sloppy Joe’s, like rare Cuban rum, has gained a richness and flavor while essentially remaining unchanged

More Fun Facts

Photo credit: Marina K. Villatoro /Gringa TravelingMom

Photo credit: Marina K. Villatoro /Gringa TravelingMom

  • In Key West, being a bastion of free thinkers even in the thirties, prohibition was looked on as an amusing exercise dreamed up by the government.
  • Even Ernest Hemingway, who lived in Key West at the time, often visited Russell’s to buy illicit bottles of Scotch.
  • Hemingway once called himself a co-owner or silent partner in the enterprise.
  • Hemingway met his third wife one drinking afternoon at Sloppy Joe’s – Martha Gellhorn.

Information to Visit Sloppy Joe’s

Reservations aren’t really necessary. You will always find a spot.

If you only have a couple of nights to spend in Key West, make sure Sloppy Joe’s is on your list of priorities.

Address: 201 Duval Street, Key West, FL 33040
Phone: (305) 294-5717