Schedule:

10 am –Key West Pride Brunch Sail & Swim. This summer we are throwing it back to the 80s! Come in your best 80s swimwear and you just might be crowned the 2025 winner of Argo's Annual Pride Cossie Contest. Whether you're channeling Miami Vice, Gloria Estefan, or the Golden Girls - make sure to bring that 80s South Florida with you! Enjoy a delicious light brunch, Bottomless Mimosas, Bloody Marys, house made Sangria and Cocktails along with Miller Lite and local craft brews aboard the Argo Navis. During our first hour, we sail along the historic Key West shoreline, giving you a great vantage point to take in the sights of the island. Then we anchor the boat and get ready for fun in the sun and playtime in the water! A portion of every ticket sold goes back to Gay Key West to help support future Pride Week activities. Argo Navis - 0 Duval St.
Ticket Link Here.

11:30 am – Pride Brunch and "Stroll Through Time" Pub Roll. Join us at our first stop and  for brunch to help soak up the libations you're about to indulge! Start your day off with an included brunch buffet and bloody mary and mimosas for an addtional fee. Then, hop on the Old Town Trolley Tour and embark on the "Stroll Through Time Pub Roll," a spirited adventure that takes you through Key West's historic and vibrant bar scene. This unique event is designed to celebrate the island's rich cultural heritage while enjoying specially curated Pride-themed drinks at each stop. Get ready to be transported back in time as you explore iconic bars outside of the Gayborhood, each offering a refreshing taste of Key West's lively atmosphere. The stroll rolls promptly at 1:00 pm. This event is 21+. Big Cheezees – 404 Southard St Limited to 75 spots; price includes brunch and pub crawl!
Ticket Link Here.

4 pm – "Generations of Strength" Street Fair and Dance Party. Step into the celebration of the "Generations of Strength" Street Fair and Dance Party, located on the bustling 700-1000 Blocks of Duval St. This joyous event is the heart of the Pride festivities, showcasing a mix of performances, eclectic vendors, and diverse community spirit. With over 50 vendors, you'll discover an array of unique crafts, delicious food, enticing drinks, and informative booths. The party doesn't stop there! Join the dance floor for live performances and Mr. Enjoy spinning electrifying tunes that will keep you moving well into the night. Whether you're exploring the fair or dancing with friends old and new, this event promises an unforgettable experience of unity and celebration. This is a family friendly event, all welcome.

7 pm – A Fabulous Evening with Lillian Baxter, Written and Performed by John Vessels & Jay Schwandt. The much loved Lillian Baxter (created and performed by John Vessels) returns with the latest chapter of her musical memoir. Join us as the fabulous (and fictional) Lillian Baxter reminisces about her life on the road less traveled. Her stories are a celebration of the nightlife, the love life, and the occasional stay at the YMCA. Your heart will thank us! 'A Fabulous Evening with Lillian Baxter’ is presented in conjunction with Key West Pride and sponsored by the Key West Business Guild. Presented (for the first time) at the Key West Armory! Fringe at the Armory, 600 White St.
Ticket Link Here!

10 pm – All Welcome Purgatory Party. Adult themed party where bad boys and bad girls come to play. Purgatory is a fetish and poolside party. Fetish attire is encouraged. This event is 21+ and has a cover charge at the door. Bourbon St. Pub – 724 Duval St.