Gay Key West
Key West Business Guild
Key West Pride Kickoff
Sunday, June 22, 2025
— — AquaPlex, 711 Duval Street
Presented by the Key West Business Guild and Gay Key West, this year's Pride event carries the overarching theme of “Still Rising.” The celebration will prominently honor the history of the LGBTQ+ community, highlighting the resilience of the LGBTQ+ movement while promoting the island's inclusive ethos of “One Human Family.” Join us at AquaPLex for this year's celebration.
Entry includes open bar, a buffet, full use of the complex, and the beats of two live DJs.
Tickets will be $25 in advance or $30 at the door.
Pride on the Move:
A Gay Key West History Trolley Tour & Pool Splash
Wednesday, June 25, 2025
— — La Concha Key West, 430 Duval St.
Celebrate Pride with an unforgettable journey through Key West’s vibrant LGBTQ+ past and present! Hop aboard our Pride History Trolley Tour, we will take you through the most iconic queer landmarks and honor the trailblazers who paved the way. Limited seating is available! But the celebration does not stop there – our final stop is the ultimate Pride Pool Splash at the newly renovated, La Concha Key West, Autograph Collection - 430 Duval St. Step off the trolley and into one of Key West's hottest pool spot for an afternoon of community, sun, and music by local Dj, Mr. Enjoy! Enjoy a full cash bar and an included BBQ buffet with an island twist made by Executive Chef, Juan Cuadra. Whether you are here to learn, dance, or simply soak it all in, this Pride experience is one you will not want to miss!
Time: 11 am Trolley Leaves promptly (limited to 38 people), Pool Splash kicks off at 12:30 pm (limited to 100 people)
Departure: Gay Key West Visitor Center - 808 Duval Street
Cost: Trolley Tour & Pool Party - $65. Price includes trolly tour, pool entry, first welcome drink, and BBQ buffet.
Pool Party only - $50. Price includes pool entry, first welcome drink, and BBQ buffet. Pool Party location: La Concha Key West, 430 Duval St.
Pride Brunch and "Stroll Through Time" Pub Roll
Saturday, June 28, 2025
— — Big Cheezees, 404 Southard Street
Join us at our first stop for brunch to soak up the libations you're about to indulge in! Start your day with an included brunch buffet and, for a nominal additional fee, unlimited Bloody Marys and mimosas. Then, hop on the Old Town Trolley Tour and embark on the "Stroll Through Time Pub Roll," a spirited adventure through Key West's historic and vibrant bar scene. This unique event celebrates the island's rich cultural heritage while you enjoy 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. Up for some COSPLAY? Come decked out in your favorite period attire, from Hippie to New Wave, to Grunge, get creative. Prizes will be awarded.
Meet at Big Cheezees at 11:30 am for brunch, trolley tour rolls at 1 pm
Tickets: $69 includes a swag bag, brunch, and pub crawl!
This event is for ages 21 and over
Tropical Heat
August 13-17, 2025
TROPICAL HEAT is Key West’s HOTTEST event for all gay, bi, queer, and trans brothers!
The temperature is not the only thing that will rise during Tropical Heat. The theme parties, pool parties, and adult-oriented entertainment promises to be HOT! August on the Island is always HOT, but during Tropical Heat it promises to be STEAMY! Five hot guys and fun days are the best way to experience Key West. Tropical Heat 2025 August 13th - 17th! Don't miss it!
With the V.I.P. band, you will receive entry or discounted entry to all parties & 5-day pass to Island House.
Tickets: $129
Buy early...prices increase to $149 on June 1st.
Womenfest Event:
5th Annual Corn Hole Tournament & Indoor Games
Thursday, September 4, 2025 — — American Legion, 803 Emma Street
Now Cooler Than Ever—Literally! We’re tossing things up this year—indoors and in the A/C! Join us for the 5th Annual Cornhole Competition at American Legion Post 168, where the bags will fly, the drinks will flow, and the vibes will be unbeatable. Whether you’re a seasoned cornhole champ or just in it for the fun, there’s something for everyone. In addition to the main tournament, we’ll have other games and activities to keep the good times rolling. Sip on cheap drinks, grab a bite from our food vendors, and enjoy a full day of friendly competition and community. Bring your best game face—and maybe a teammate or two. Let’s make this year the most fun yet!
Team Tickets: $50
Womenfest Event:
Decades of Divas 80’s Prom
Saturday, September 6, 2025 — — American Legion, 803 Emma Street
DJ Rude Girl is back and will be providing the tunes all night long! Hosted by the glittery empress, Chantal P. Big Hair, Bold Looks, and All the Diva Energy You Can Handle! Get ready to step back into the most glam, outrageous, and fabulous decade of them all! Join us for Decades of Divas: 80’s Prom—a night where neon reigns, glitter rules, and everyone is the star of their power ballad. We’re talking teased hair, shoulder pads, and dance moves that don’t quit. Dress to impress in your best 80’s diva attire—Madonna, Whitney, Donna Summer, or full-on prom queen realness. We’ll have a photo booth, themed cocktails (and mocktails!), and a playlist packed with 80’s hits to keep you dancing all night long. It’s your time to shine—so grab your date, your crew, or fly solo and strut into prom like the icon you are.
Tickets: $40