Fantasy Fest 2026 Returns for 2026 with ‘Musical Icons and Iconic Music' Theme

Fantasy Fest is set to return to Key West in the Florida Keys from 16-25 October. The annual festival is a staple in the island city’s events calendar. The 10-day long costuming party in paradise welcomes revellers from near and far to turn the island into a living celebration of musical spectacle.

The 2026 Fantasy Fest theme, ‘Musical Icons and Iconic Musicals’ invites fantasy-makers to style themselves at the centre of a Ziegfeld extravaganza, follow the call of a disco ball, go Gaga for Ziggy Stardust, embody the Mercury magic, or take centre stage as the musical icon – or iconic musical character – of their dreams. The sky’s no limit for this ‘Swift-ly’ moving and ‘Wicked-ly’ wondrous multi-day escape from the ordinary.  

“At Fantasy Fest, you can see the spectacle and be the spectacle,” said Fantasy Fest Director Nadene Grossman Orr. “Whether you arrive as a Broadway legend, rock icon, pop superstar, or icon of your own creation, this is your invitation to step into the spotlight and let your imagination take flight.”

Below is a sampling of just some of this year’s festival event highlights:

- 16 October: The Royal Coronation event to crown Fantasy Fest’s 2026 King and Queen is a dazzling two-hour stage show with performances by the intrepid competitors along with local celebrities

- 16 and 17 October: The Bahama Village Goombay Festival is a two-day, family friendly celebration of island arts and crafts, culture, music and food held throughout Key West’s historic Bahama Village neighbourhood

- 18 October: That Arena Rock Show at Sunset Pier: A free admission, high-energy, time-travelling theatrical tribute to classic Rock & Roll

- 19 October: A Green Parrot Beatles Tribute: Jump into your yellow submarine and disembark in the 1960’s for this dress-up dance party with Key West’s very own Beatles tribute band

- 20 October: Tutu Tuesday with its annual epic dance party features lights, lasers, and multiple dynamic DJ’s spinning at four different Caroline St. district area venues. Tutu’s required!

- 21 October: LUV2GLOW PARTY: Rick’s Upstairs on Duval Street transforms into a vibrant universe of fluorescent visuals, underwater-inspired décor, and pulsating house music with immersive glowing environments, DJ’s and live performers. Come dressed or painted to glow under black lights. This year’s theme is LIQUID FREQUENCY

- 21 October: Pet Masquerade: Costume up with your favourite critter friends at this over-the-top competition or cheer them on from the audience

- 22 October: The 42nd Annual Key West Headdress Ball reveals a playlist of out-of-this-world headdresses modelled by their creators along with high-energy entertainment by some of the island’s best talent

- 22 October: Sloppy Joe’s 47th Annual Toga Party: Live music starts early and flows late at this revelry, where fantasy-makers can don traditional Roman ‘drape duds’ or create their own 2026 Fantasy Fest theme-inspired versions. Toga costume contest welcomes individuals or groups of 2-4

- 23 October: Paparazzi Row is the place to get warmed up and strut your stuff for the camera’s ahead of the Captain Morgan Masquerade March. Dance music will play and local paparazzi, photo booths and selfie stations will be set up to record epic costumed crews

- 24 October: The world-famous Deep Eddy Vodka Fantasy Fest Parade in Old Town Key West presents a dazzling array of fabulous floats, magnificent marching groups, and cool kinetic contraptions to bring this year’s ‘Musical Icons and Iconic Musicals’ theme to life. An awesome island tradition since 1979!

- 25 October: Don your fabulous feathers for ‘The Fat Lady Sings’ Tea Dance at La Te Da on Duval Street—the final official Fantasy Fest celebration

- 26 October: The 2026 Fantasy Fest theme will be announced

For a full calendar of events, schedule updates, contest details, and a downloadable mobile APP, visit FantasyFest.com www.fantasyfest.com.

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Photo Caption: The spectacularly creative annual Headdress Ball is set for Thursday, 22 October. Photo Credit: Carol Tedesco/Fantasy Fest. Additional high-resolution images are available HERE.

About The Florida Keys & Key West: A premier getaway destination located at the southernmost tip of Florida and the continental United States. The Keys stretch over 125 miles connected by 42 bridges and bordered by the Atlantic Ocean and the Gulf. Discover the spectacular array of diverse activities offered in the Florida Keys like fishing, diving, natural wonders, fine dining, and cultural heritage. From large resorts, secluded waterfront hideaways and courtyard guest houses, visitors can uncover the perfect place for their holiday. Restoration, renovation and preservation have become a way of life in the Florida Keys. Whether you’re driving or flying into the Keys, one thing is for sure: there’s simply no place quite like it.