Fantastic Festivals Kick-off Fall in the Florida Keys & Key West

Womenfest, 6-10 September - One of the largest gatherings of LGBTQ women in the USA

Big Gay Key West, 13-18 September – Inaugural Big Gay Key West festivities

Fantasy Fest, 20-29 October - Unicorn-like Uniqueness & 200th anniversary of the Keys


August 2023: There’s plenty to look forward to in the Florida Keys this autumn as the USA’s southernmost city Key West celebrates its party town reputation with three spectacular events.

One of North America’s largest gatherings of LGBTQ women is to take place in Key West from 6-10 September, featuring vibrant festivities that only the welcoming island city can offer. Womenfest 2023 is to feature an exhilarating lineup of activities and parties designed to cater to virtually every girl’s desires. With a history dating back more than 20 years, the festival strives to foster camaraderie between like-minded women, while also showcasing the attributes that make Key West an internationally acclaimed lesbian and gay vacation destination.

Highlights include the Women, Words & Art Poetry Reading and Art Exhibition at The Little Room Jazz Club on Duval Street; a sunset sail aboard the luxury vessel Argo Navis; and the star-studded 2023 debut of The Girly Burly Burlesque Show at the Key West Theater on Eaton Street.

Festival attendees can explore Key West and learn about the island’s influential women on a fun-filled Key Lime Bike Tour, and end their weekend the “Key West way” with two island city traditions: the adults-only Mangoes Sunday Drag Brunch at noon, combining stellar entertainment and delicious brunch options, and the original Sunday Tea Dance at legendary La Te Da on Duval Street.

Then from 13-18 September, Key West is set to host the inaugural Big Gay Key West festivities, an adult-oriented LGBTQ event with a “cabana boy” theme. Attendees can look forward to pool parties, clothing-optional events, late-night adventures, and gatherings that showcase some of the island’s leading LGBTQ venues. There will also be the chance to venture out and enjoy other land and water adventures that Key West has to offer.

In October, fans of the Florida Keys’ quirky creativity and whimsical spirit can celebrate both, as well as the island chain’s 2023 bicentennial, during Key West’s annual Fantasy Fest.  An internationally renowned costuming and masking festival, Fantasy Fest takes place from 20-29 October. The revelry includes masquerade balls, costume competitions, glamorous galas and an over-the-top grand parade. Imaginative costuming is paramount, with the best efforts drawing acclaim and applause.

The 2023 festival is themed “Uniforms and Unicorns…200 Years of Sailing into Fantasy” to salute the Keys’ bicentennial and that of the U.S. Navy in Key West, as well as the island chain’s “unicorn-like” individuality and mystical appeal.

The official kick-off is the two-day Goombay Festival, which pulses to a Caribbean beat with nonstop music, arts and crafts, and island-style food. Among dozens of events awaiting attendees is the wacky Pet Masquerade, a Fantasy Fest favourite for costumed pets and their people that takes place on 25 October. The following night brings the 40th anniversary Headdress Ball, where entrants compete for “head-turning” prizes in huge and elaborate masks and cowls. Then unicorns and uniformed partiers are invited to strut through the streets on 27 October, during the Captain Morgan Masquerade March. Other highlights include the family-friendly Zombie Bike Ride, rocking Beatles tribute show and look-alike bash, Tutu Tuesday and pool parties, waterfront Woodstock take-off, music and art showcases, and lively Fantasy Market.

The night of 28 October sees tens of thousands of spectators line Whitehead and Duval streets in Key West’s historic downtown for the Bud Light Fantasy Fest Parade. A dazzling procession of large-scale floats, costumed marching groups and bands, the parade illustrates the creativity and spirit that have helped define the Florida Keys for the past 200 years.  

Credit_Florida Keys News Bureau

Credit_Florida Keys News Bureau

This article was updated on January 30, 2024 at 7:15 AM