September 3-7th, 2025

Womenfest 2025: Decades of Divas
Five Days of Celebration in Paradise! Get ready to turn up the volume and celebrate bold, brilliant, and iconic women through the ages! Womenfest is back for another unforgettable year in paradise—five days of connection, empowerment, and celebration designed by women, for women. This year’s theme, “Decades of Divas,” honors the legendary trailblazers, pop culture queens, and everyday divas who’ve shaped our lives—from disco to digital, retro to revolutionary. Expect dazzling themed parties, soulful music, inspiring workshops, poolside fun, and the kind of community that makes Womenfest truly magical. Whether you’re channeling your inner Taylor Swift, Meg The Stallion, Madonna, Beyoncé, or your own personal diva, Womenfest is the place to shine.
Mark your calendar, gather your crew, and come celebrate the divas of every decade—especially you.
Womenfest 2025 — Decades of Divas
Schedule of Events
Noon – 1 pm — Key West Business Guild Membership Luncheon. Our September Luncheon is proudly sponsored by Mount Sinai Medical Center. Please join us as we open Womenfest celebrating the “Decades of Divas”! Featuring a conversation and special performance by our local diva, Terri White. *Non-profit Spotlight is Samuel’s House presented by, Maria Protopsaltis – Deputy Director at Samuel’s House. Entry for KWBG members are $35, non-members are $45. Beachside Resort & Residences Key West – 3841 N Roosevelt Blvd. RSVP Here!
6-8 pm — WOMENFEST 2025 — Decades of Divas! Our official Welcome Party Birdcage Cabaret. Join us for an evening of meeting new friends and reconnecting with old ones in a vibrant and welcoming atmosphere to kick-off to Womenfest, hosted by the glittery empress, Chantal P. Enjoy games, live music, drink specials, and small bites! Birdcage Cabaret – 504 Angela St.
8:30 pm — Womenfest Edition Drag Show at Birdcage Cabaret – 504 Angela St. Stick around for a drag show designed specially for Womenfest Kick-off Party! More details to come.
12 – 3 pm — 5th Annual Corn Hole Tournament & Indoor Games. 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 affordable drinks, grab a bite from the bar, 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! Sign up Here. American Legion Post 168 – 803 Emma St.
- $3 domestics
- $4 imports
- $4 well drinks
- Funky Beats & Retro Vibes – think Donna Summer, Bee Gees, and a dash of glitter.
- FREE Disco Swag Bags– disco necklaces, disco key chains, 70’s glasses, and tons of your favorite 70’s sweet treats! 💃 Dress Code: Disco flair encouraged. Bell bottoms optional, sparkle mandatory. 📍 Location: Bobby’s Monkey Bar, Key West – The grooviest joint in town!
✨ Come for the drinks, stay for the boogie.🪩 Bobby’s Monkey Bar – 900 Simonton St.
6 pm — Third Annual “Women, Words, & Art Poetry Reading and Art Exhibition” featuring women poets of the Key West Poetry Guild and local artists. To open the show, bring your own memories and make some new ones as we journey back in time to the vibrant beginnings of Womenfest in Key West with a presentation by Susan Kent. Discover the stories, the people, and the enduring spirit that shapes this iconic celebration of women, transforming a local initiative into one of the largest gatherings of lesbians and their friends in North America. Explore how the event evolved and adapted, becoming a vital part of Key West’s unique LGBTQ+ history and attracting women from all walks of life to celebrate camaraderie and freedom in paradise. To follow, a combination of round-robin and open mic readings. This event will feature approximately 8 woman poets reading poetry in a round-robin fashion with an open mike session also. Jah Love of the Key West Poetry Guild will be hosting the poetry reading portion. At the same time, we will have an art display by women artists. Connie Gilbert Scholarship Fund – The Connie Gilbert Scholarship Fund is to benefit women in the Florida Keys who are returning to school from the workforce, seeking professional licensing or certification, or have completed at least one year of higher education. Tropic Cinema –416 Eaton St.
*SOLD OUT * 6 pm — Argo Navis presents the annual Womenfest Sunset Sail featuring the local diva and songstress, Michelle Dravis. Hosted in conjunction with the Key West Business Guild, is part of a 5-day island wide celebration of women worldwide! Join us for 2 hours of sailing the magical green waters where the Atlantic Ocean meets the Gulf of Mexico. Combine this with delicious food & drink, tropical breezes and the soothing sound of wind and waves as the sun sinks into the horizon, leaving us with a glorious show of color in the sky. Argo Navis Key West Sailing Charters – 0 Duval St.
9 pm — GrEEEn 60’s/70’s Hippies Party. Enter a world celebrating all things greeen! Dress in your best greeen hippie attire and dance the night away with the island’s best go-go dancers! Sponsored by the Greeen House – We spell it with 3 E’s so that you can’t say it without smiling, and that’s the goal, right?Birdcage Cabaret – 504 Angela St.
8-9 am — Early Bird Clean Up with Plogging the Keys, presented by Key West Womenfest. Join us for 1 hour to pick up litter. Vests, gloves, buckets, and pickers are provided. One hour makes a difference in keeping Key West Beautiful. Meet us at 808 Duval Street at the Gay Key West visitor center. Bagels, danish, and coffee will be provided by Goldman’s Deli afterward!
9:30 AM-11:30 PM— Join Key Lime Bike Tours for an unforgettable journey through the streets of Old Town Key West, a tour specially designed for Womenfest celebrating influential women! On this tour, you will discover the rich history and culture of Key West, while learning about the remarkable women who have made an impact on this beautiful island. Our knowledgeable and friendly guide will lead you on a leisurely bicycle ride through the charming streets of Old Town, stopping at significant landmarks and hidden gems along the way. As we ride through the picturesque neighborhoods and historic sites, you’ll hear stories of remarkable women who have called Key West home. At the end of your tour, we’ll finish with a delicious slice of Award Winning Key Lime Pie! Purchase tickets HERE.
11 am — Clothing optional Sandbar Snorkel trip on the Blu Q. We will set sail on the Blu Q Catamaran to one of many remote reefs off the Florida National Marine Sanctuary for snorkeling with tropical fish and various marine life. Afterward, you are taken to a secluded sandbar where you can swim, or just relax in the crystal clear waters of the Keys. Get 10% off with the code WomenFest25. Purchase tickets HERE.
12 pm — All welcome pool party – Bourbon St. Pub – 724 Duval St.
2 – 4 pm — Y2K Jell-O Wrestling Match hosted by your referee, BruceKey @AquaPlex. Watch as participants take to the ring for some friendly, competitive Jell-O wrestling. Enjoy a fiery, high energy atmosphere, cool AC and ice cold drinks available! **This is strictly a private event and only reserved for Womenfest participants. Wanna be a participant? Please email BruceKey at [email protected]
3:30 – 5 pm —🌩️Love in A Flash⚡: A Sapphic Speed Dating Experience. Get ready to spark connections in a flash! Join us for an electrifying afternoon of sapphic speed dating designed for women who love women. Whether you’re looking for love, laughter, or just a new friend, this is your chance to meet incredible people in a fun, low-pressure environment. Expect quickfire conversations, cheeky icebreakers, and plenty of opportunities to find your next crush—or maybe something more. Come as you are and leave with butterflies… or at least a great story.
✨ Open to lesbian, bisexual, queer, pansexual, trans, and questioning women
✨ Fun prompts to keep the convo flowing
✨ Cocktails, mocktails & mingling after rounds
Because sometimes, all it takes is a spark. Let love strike. ⚡Entry is a donation at the door. To participate, sign up HERE
5 – 6:30 pm — Marjory Lee & The Misspellings “90s Female Alt Rock Band” Blast to the past Cover Show! Alanis, Gwen, Melissa, Sheryl, Fiona, Tracy, Joan…..gangs all here! Don’t miss this tribute to the badass female musicians of the 90s and all the closet doors they kicked down! Marjory Lee is a full-time local musician in Key West bringing ALL the lady love you can handle. Free event. RamHead Southernmost – 804 Whitehead St.
10:00–11:30 AM | Womenfest Fragrance Making Class. Smells Like Teen Spirit. Create your own signature scent in this hands-on, guided perfume-making class inspired by the Decades of Divas. With access to over 300 oils from our luxury fragrance organ, you’ll blend, mix, and layer your way through the eras to craft three custom fragrances—then bottle your favorite in true diva style. Whether you’re channeling disco glam, 80s edge, or 90s grunge, this experience is all about expressing your era through scent. Tijon Key West – 335 Duval Street, Suite E. Your experience includes:
• A 55ml bottle of your personalized fragrance
• A VIP Tijon gift bag (valued at $60)
• A class certificate to mark your creative journey
• And of course, a champagne toast to celebrate your inner icon! Reserve your spot Here! This event is limited.
12-3 PM — Join us for the Official Womenfest Pool Party at Lighthouse Hotel hosted by the fabulous BAM with DJ Erika, who will be turning up the heat. Soak up the sun while dancing through the decades!
🧉 Start the fun with a complimentary Bad Bitch Rum cocktail—because your poolside presence deserves a proper toast.
🎟️ Enter our raffle and score some seriously fun giveaways benefitting a great cause.
🎯 Enjoy games like our famous water balloon toss, poolside challenges, and more—because this party doesn’t just float, it slays.
Bring your best suit, boldest energy, and a few friends ready to party. Let’s make waves, divas! – Lighthouse Hotel – 902 Whitehead St
3 PM —Rainbow History Trolley Tour — Womenfest Edition: Celebrate Womenfest with an unforgettable journey through Key West’s vibrant LGBTQ+ past and present! Hop aboard our Rainbow History Trolley Tour, we will take you through the most iconic queer landmarks. and fully narrated by expert tour conductor – SKIPPPER. Ticket link HERE.
8 PM— Decades of Divas 80’s Prom. Dress to impress in your best 80’s diva attire—Madonna, Whitney, Prince, or full-on prom queen realness. We’ll have a photo booth, themed cocktails (and mocktails!), and DJ Rude Girl is back providing the 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! Hosted by the glittery empress, Chantal P. Join us for Decades of Divas: ’80s 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! American Legion Post 168 – 803 Emma St. Tickets Here
11 PM— Decades of Divas 80’s Prom Afterparty @ the Birdcage Cabaret – 504 Angela. There’s no need to change, just join us after the Decades of Divas 80’s Prom for the perfect way to cap off an incredible evening!
Noon pm —“You CAN Sit With Us” Drag Brunch: We are excited to announce that we will be adding 25 more seats at the bar! **Please note that these seats are located in a separate area and may have limited visibility. Performers will be walking through the entire space to be sure you are part of the show, but your view will be obstructed. The price for these seats will be slightly lower at $40. Hosted and produced by Beatrix Dixie. Join us for a fabulous Drag Brunch from 12–3 PM, with dazzling performances including drag kings! Enjoy a vibrant afternoon of entertainment, laughter, and a delicious buffet featuring shrimp bisque, French toast with berries, eggs, bacon, sausage, home fries, cured salmon, benedicts, jerk chicken with yellow rice, croissants, fresh fruit, salad, and sweet treats like flan and key lime pie. Ticket link is HERE! You can also reserve your spot and purchase your tickets by contacting Fritzie at (305) 294-4603 or [email protected]. Key West Cooking School & Bar – 291 Front Street (inside The Shops of Mallory Square up the escalator).
This event is All Welcome and 21+.
3 pm — Hot Dog Church. If you’re looking for a laid-back atmosphere to break from all the partying you did all week, then this is the place for you! Yes, there will be hot dogs, there will be games, there will be chill vibes!
4 pm — The Original Tea Dance – a Key West Tradition. Join us for the last dance to close out Womenfest 2025 @La Te Da featuring DJ Rude Girl.
Museums: Key West Art & Historical Society, Ernest Hemingway, Key West Butterfly Conservatory, Little White House, Key West Aquarium, Mel Fisher Maritime Museum, Key West Firehouse Museum, Key West Light House, Key West Ship Wreck Museum, Audubon House, Oldest House and Garden Museum, USCGC Ingham Museum, Tennessee Williams Exhibit.
Land Activities: Key West Food Tours, Key West Cooking School, Fort Zachary State Park, West Martello Tower, Key West Tropical Forest and Botanical Garden, Key West Cemetery, Key West Adventures, Papa’s Pilar Rum Distillery, Ghost Hunt, Old Town Trolley Tours, Conch Tour Train, Haunted Key West, Ghosts and Mysteries, Ghosts and Gravestones, D’vine Wine Gallery.
Water Activities: Blu Q, Classic Harbor Lines, Cruisin’ Tikis, Danger Charters, Fish N Chicks, Fury, Island Vibe Charters, Java Cat, Jolly Rover II, Key West Eco Tours, Key West Sailing Center, Key West Snorkeling. Land Boat Charters, Off the Charts, Schooner America, Sunset Sail Key West, Sunset Watersports, SV Argo Navis, Yankee Freedom.
Future Womenfest Dates
2024: 9/4 - 9/8
2025: 9/3 - 9/7
2026: 9/2 - 9/6
2027: 9/1 - 9/5
2028: 9/6 - 9/10






















































