Events

March 2023

Welcome Spring Breakers

Sloppy Joe’s 42nd Annual Hemingway® Look-Alike Contest July 20-22, 2023.

WEDNESDAY, JULY 19, 2023

5:00 pm Meet the “Papas” at Sloppy Joe’s. Get to know the contestants and previous winners of “Sloppy Joe’s Hemingway® Look-Alike Contest.

THURSDAY, JULY 20, 2023

6:00 pm Hemingway Look-Alike Society scholarship presentations. The society is to announce the winners of its annual scholarships for Florida Keys students. On stage at Sloppy Joe’s Bar.

6:30 pm Sloppy Joe’s 42nd Annual Hemingway® Look-Alike Contest – Preliminary Round One on stage at Sloppy Joe’s. Approximately 75 contestants will be narrowed down to approximately 12 finalists to advance to Saturday night’s final round.

FRIDAY, JULY 21, 2023

6:30 pm Sloppy Joe’s 42nd Annual Hemingway® Look-Alike Contest – Preliminary Round Two on stage at Sloppy Joe’s. Approximately 75 contestants will be narrowed down to approximately 12 finalists to advance to Saturday night’s final round.

SATURDAY, JULY 20, 2023

Noon Photos with “Papas.” Hemingway® Look-Alikes provide a photo opportunity for fans. Greene Street outside Sloppy Joe’s.

1:00 pm Running of the Bulls. This wacky event is sponsored by Sloppy Joe’s Bar and features past “Papa” Hemingway® Look-Alike Contest winners dressed in their Pamplona best — and a breed of “bull” found only in Key West. The fun takes place on Greene street outside Sloppy Joe’s.

HLAS will sell red berets and red bandanas (limited quantities) beginning at 12 Noon on Saturdays. Those wishing to wear tradition white clothing with red sash need to be prepared and bring their own clothing (these items not sold).

6:30 pm Sloppy Joe’s 42nd Annual Hemingway® Look-Alike Contest – FINAL ROUND to name Papa 2023.

October 2023

October 20-28, 2023 Fantasy Fest 2023 “Uniforms & Unicorns.”

Sunday, October 22, 2023 – SLOPPY JOE’S ZOMBIE DANCE PARTY
Come dressed as your favorite Zombie and dance all night.

Monday, October 23, 2023 – SLOPPY JOE’S COMIC BOOK CAPE-ERS PARTY
OFFICIAL FANTASY FEST EVENT – Come dressed as your favorite “Caped” Superhero or Supervillain and party all night. Live music on stage all day!

Wednesday, October 25, 2023 – SLOPPY JOE’S SLUMBER PARTY

OFFICIAL FANTASY FEST EVENT… Roll out of bed and head on over to Sloppy Joe’s Slumber Party. Be creative. Be goofy. But be dressed in a costume…will it be… a onesie, flannel jammies, boxers or your favorite lingerie. Create your outfit around Fantasy Fest Theme “Uniforms & Unicorns” (a costume you can wear all week). Spend the day and/or night partying and dancing in comfort at Sloppy Joe’s.

Thursday, October 26, 2023 – SLOPPY JOE’S 44th ANNUAL TOGA PARTY
AN ORIGINAL FANTASY FEST EVENT – Sloppy Joe’s Toga Party is “An ORIGINAL Fantasy Fest Event.” Get your toga ON and find out why we are “Still The Best Toga Party in Town!” Wear a traditional ancient Toga or dare to create your Toga using Fantasy Fest theme “Uniforms & Unicorns ”

Saturday, October 28, 2023 – Fantasy Fest Parade
Come dressed in costume and party all day and night! And catch the parade here.

November 2023

Welcome POWER BOAT RACE FANS November 5-12, 2023!

Sloppy Joe’s is an official sponsor of the Key West Race World Offshore Power Boat Races November 5-12, 2023.

November 5th Boat parade down Duval Street at 4:00pm

November 10th 7:30pm-10:30pm Duval & Greene Street Power Boat Street Party.