Live Music and Legendary Fun at Sloppy Joes Key West

When learning about all the different places to visit in Key West, Sloppy Joe’s Bar is probably one of the most legendary and traditional of all.

sloppy joes key west

When I contacted Sloppy Joe’s, they recommended if you come with kids it would be better to come for lunch, at night it turns more into a live music nightclub with food. (Note after 9:30pm customers must be 21 years old).

Finally, for the first time in years, I was able to say it will be an adults night out (our mini-honeymoon) and we can enjoy live music and drinks.

Sloppy Joe’s is located on the fun side of Duval Street. When I say fun, this is where all main action takes place like bars, restaurants and tons of foot movement on the streets checking out all the shops.

duval street key west

We arrived to the restaurant at 6 pm and it was PACKED! I was so surprised and excited. It says to seat yourselves, but with all the commotion, I asked for help from the staff and they put us right in front of the stage. That evening it was a live music act by Pete and Wayne, which seemed to be a tradition in itself. They have been performing here for almost twenty years.

Key West, Florida- Sloppy Joe's - live music

Maybe I don’t get out much, but they were so much fun! Their skits and songs were ingenious and racy. Exactly what I needed.

How To Enjoy Sloppy Joes Key West 

When planning to come to Sloppy Joe’s, allot several hours. This is not the type of place to eat and run. And if they have a good act going on, you probably want to spend the full night there.

Key West, Florida- Sloppy Joe's

Even though they are best known for their Sloppy Joe sandwiches, which Ernest Hemingway recommended naming the place after, you don’t really come here to eat.

Key West, Florida- Sloppy Joe's - sloppy joe dish

You come here for the yummy drinks and a great atmosphere.

Key West, Florida- Sloppy Joe's - drinks up

Video Fun

History of Sloppy Joe and Key West

  • The official beginning of Sloppy Joe’s Bar, the famous and infamous Key West saloon, was December 5, 1933–the day Prohibition was repealed. But it had already been around for a while.

  • The bar was destined to go through two name changes and a sudden change of location before it would become Sloppy Joe’s.

  • It’s first name was  Joe Russell, but later became the Silver Slipper when a dance floor was added. But the name wasn’t well taken.

  • It was Hemingway, a favorite patron of Russell’s bar from the start, who encouraged its name change to Sloppy Joe’s.

  • Over the years Sloppy Joe’s, like rare Cuban rum, has gained a richness and flavor while essentially remaining unchanged

  • 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–customers simply picked up their drinks and carried them, along with every piece of furniture in the place, down the block to 201 Duval Street.

  • The new Sloppy Joe’s boasted the longest bar in town.

  • When Hemingway left Key West in 1939, he left a number of personal effects 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.

Key West, Florida- Sloppy Joe's - ernest hemingway and fidel castro

  • Joe Russell died in 1941 of a heart attack.  He was 53 years old.

  • Hemingway’s stuff remained there until 1962, a year after Hemingway’s death, when 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.

More Fun Facts

  • 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 made Key West his home at the time, slipped over to Russell’s on occasion 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

No reservations are taken, tables first come basis. You will always find a spot inside either by the bar, tables or standing room at the back of the restaurant.

Key West, Florida- Sloppy Joe's - bar

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

 

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About Marina Kuperman Villatoro

Marina Kuperman Villatoro CEO of TravelExperta.com, a travel resource site to inspire families to travel with kids of all ages. Marina has been an expat 10+ years in Central America raising 2 boys in a multicultural, trilingual household. She travels all over the world with her family to give first hand experiences of where to eat, stay and play with kids. Needless to say, it’s never boring! Join Marina on Facebook and Twitter for more unique and boutique family travel!

2 Responses to Live Music and Legendary Fun at Sloppy Joes Key West

  1. That looks like a very lively restaurant! It looks like you had a lot of fun. Thanks for all of the information!
    Mary @ Green Global Travel recently posted..Announcing Our Next Big Adventure!My Profile

  2. Jennifer says:

    I’ve never had sloppy joes at a restaurant and they are so delicious that now I’m trying to figure out why more restaurants don’t serve them! Looks like a fun and lively spot.
    Jennifer recently posted..5 Vino Vacations to Take This SummerMy Profile

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