Events
Check out Sloppy Joe’s Daily Entertainment Calendar, click here.
October 2023
October 20-28, 2023 Fantasy Fest 2023 Theme “Uniforms & Unicorns.”
Sunday, October 22, 2023 – SLOPPY JOE’S MONSTER BASH & GRAVEYARD GROOVE
Come dressed as your favorite zombie, monster or graveyard character. Graveyard dance contest sign up next to stage at 8:15pm, dance contest on stage at 9:00pm (must be in costume). Prizes: 1st place $100 Sloppy Joe’s Gift Card; 2nd place $50 Sloppy Joe’s Gift Card; and third place $25 Sloppy Joe’s Gift Card. Live Music all day, Turning The Tide on stage following dance contest.
Monday, October 23, 2023 – SLOPPY JOE’S COMIC BOOK CAPE-ERS COSTUME CONTEST
OFFICIAL FANTASY FEST EVENT! Come dressed as your favorite “Caped” Superhero or Supervillain and party all day and night. Live music on stage all day! Dancing starts at 5:30pm, Turning The Tide on stage following contest, plus our house DJ will keep you dancing all night. To enter costume contest sign up next to stage at 8:15pm, contest on stage at 9:00pm. You may enter contest as an individual or as a group of 2-4 people (must be in costume). Prizes: 1st place $500 Sloppy Joe’s Gift Card; 2nd place $250 Sloppy Joe’s Gift Card; and third place $100 Sloppy Joe’s Gift Card. Other giveaways throughout the night. Sloppy Joe’s 201 Duval Street.
Wednesday, October 25, 2023 – SLOPPY JOE’S SLUMBER PARTY COSTUME CONTEST
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). To enter costume contest sign up next to stage at 8:15pm, contest on stage at 9:00pm. You may enter contest as an individual or as a group of 2-4 people (must be in costume). Spend the day and night partying and dancing in comfort at Sloppy Joe’s. Prizes: 1st place $500 Sloppy Joe’s Gift Card; 2nd place $250 Sloppy Joe’s Gift Card; and 3rd place $100 Sloppy Joe’s Gift Card. Other giveaways throughout the night. Sloppy Joe’s 201 Duval Street.
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 ” Live music on stage all day! Dancing starts at 5:30pm, M80 on stage after Toga contest, plus our house DJ make the party happen all night. Sign up for Toga Contest 8:15pm, contest on stage at 9:00pm. You may enter contest as an individual or as a group (a group is a minimum of 2 people and maximum of 4 people) must be in Toga(s). Prizes: 1st place $500 Sloppy Joe’s Gift Card; 2nd place $250 Sloppy Joe’s Gift Card; and 3rd place $100 Sloppy Joe’s Gift Card. Other giveaways throughout the night. Sloppy Joe’s 201 Duval Street.
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.
December 2023
December 3, 2023 Sloppy Joe’s all-day Flapper Costume Party to celebrate the End of Prohibition. Come dress in costume of the 30s and party all day. More information to come.
December 5, 2023 End of Prohibition stop by and celebrate 90 years of booze and beer!
December 31, 2023 New Year’s Eve – Sloppy Joe’s 30th Annual Dropping of the Conch Shell.
Inside Live music on stage noon-2:00am. Outside live from the roof, Sloppy Joe’s Annual Dropping of the Conch Shell starting at 10:00pm.
No reservations taken on New Year’s Eve, tables are first come basis.
Photo by Carol Tedesco
May 2024
May 5, 2024 Sloppy Joe’s celebrates 87 years at the corner of Duval and Greene.
Photo: Sloppy Joe’s Bar and Cabaret on Duval Street, Key West. The DeWolfe and Wood Collection.
July 2024
Sloppy Joe’s 43rd Annual Hemingway Look-Alike Contest July 18-20, 2024
More information and schedule of events to be announced.