Womenfest: Events

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.

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 Link 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. @Little Room Jazz Club. 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.

6 pm — Argo Navis presents the annual Womenfest Sunset Sail featuring the local diva and songstress, Claire Caplan. 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?

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! Ticket link coming soon!

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

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]

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. More info comeing soon!

9 pm – 2 am —Pink Paradise Dance Party @Mangoes . Entry is just $20 per person – includes entry and your first drink. Dress in your best pink attire and join us for a unforgettable night of music, dancing, and pure joy – celebrating women. Don’t miss out on the ultimate ladies night out! This is a 21+ event. Ticket link coming soon!

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! Register HERE.

12-3 pm — “Kat & Beth’s Are you Wet Pool Party” @Alexander’s Guesthouse – HOST HOTEL with guest DJ. We have a special pool party lined up for you ladies! Kat D and Beth are BACK! She will be joined by guest DJ Erica to offer you the latest hits along with drink specials, complimentary food, games, and prizes!

8 PM— Decades of Divas 80’s Prom. 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 own 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, Prince, 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. American legion Post 168 – 803 Emma St. Ticket link 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!

12 pm — Celebrate Key West Style! Mangoes Sunday Drag Brunch Show has been voted the Top 10 Drag Brunch Show in the USA. VIP tickets & General Admission tickets include: a fabulous show with incredible Drag Queens, a live DJ, amazing entertainers, and bottomless mimosas. Mangoes offers a special a la carte brunch menu with delicious brunch specials available. Stay for the After Party to get your picture taken with our beautiful drag queens and keep dancing to DJ Jeff’s tunes. A portion of each ticket sold will go to our nonprofit partner for this month. THIS EVENT IS A 21+ EVENT, NO ONE UNDER 21 PERMITTED. NO REFUNDS. DOUBLE CHECK THE DATE BEFORE YOU CLICK PURCHASE – TICKETS ARE NON-REFUNDABLE. Ticket link coming soon.

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.

3–6 pm —Alyssa Goldstein performing daily during Happy Hour for the week of Womenfest, acoustic music spanning decades and genres for the last 30+ years at AquaPlex.

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.