September 3rd-7th 2025, Key West Womenfest!
Womenfest has attracted a diverse group of woman since its inception decades ago. The festival offers a wide range of activities for those who want to socialize, feel comfortable being themselves, soak up some sun, then party, laugh and dance the night away.
September 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.
Schedule of Events
Wednesday, September 3
Noon – 1 pm — Key West Business Guild Membership Luncheon. Join us at the Beachside Resort & Residences Key West – 3841 N Roosevelt Blvd. Speaker & sponsor TBD. Entry for KWBG members are $35, non-members are $45. More details to come.
6-8 pm — WOMENFEST 2025 — Decades of Divas! Our official Welcome Party Birdcage Caberet. 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!
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.
Thursday, September 4
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 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! Sign up Here. American Legion Post 168 – 803 Emma 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. 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.
6 pm — Argo Navis presents the annual Womenfest Sunset Sail featuring the local diva and songstress, TBD. 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. Book your spot HERE!
9 pm — Greeen 60’s/70’s Hippies Party at the Birdcage Cabaret – 504 Angela St. 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?
Friday, September 5
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 WomenFest24. 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 brucekey6969@gmail.com
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 Soutthernmost – 804 Whitehead St.
Saturday, September 6
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 — We have a special pool party lined up for you ladies! Details coming soon! Location TBD.
3 PM —Old Town Trolley Tour — Womenfest Edition: Old Trolly Tour. Join us for Key West’s most comprehensive tour, covering over 100 points of interest and fully narrated by expert tour conductor – SKIPPPER. More details to come with ticket link.
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!
Sunday, September 7
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.
Daily Activities
Museums: 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, Up the Keys Eco Tour, 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.
