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16 Best Events of Fantasy Fest 2023

Posted on: September 15th , 2023 | Events & Festivals
16 Best Events of Fantasy Fest 2023

Fantasy Fest 2023 runs Oct. 20 - 29, and there’s so much planned for this year’s theme of “Uniforms & Unicorns: 200 Years Of Sailing Into Fantasy” that it’s hard to keep tabs on the must-see attractions. In addition to the always popular Fantasy Fest Parade, there are plenty of standout events we have our eye on. Check out the Fantasy Fest schedule to see all there is to enjoy this year and read on for the top events of 2023.

Although we strive to provide the most current information, events mentioned may be canceled without notice. We recommend checking the official Fantasy Fest website for updates before visiting.

[Stay tuned for our 2023 iteration of 'All Things Fantasy Fest', coming soon]

But first, What’s New to Fantasy Fest 2023:

The first ever Fantasy Beard Contest makes its debut at General Horseplay on Mon. Oct. 23. From 4 - 8 p.m., watch the “greatest beard show on earth” and see “exotic beards of all types” on stage for a pageant like no other. Can’t grow one? There’s a special category for those who make or buy one. Also new this year, musical acts The Black Crowes (7 p.m. at Coffee Butler Amphitheater) and The Wailers (8 p.m. at Key West Theater) set up for special performances Thurs. Oct. 19, and the first ever Rock on With Your Smock On: Fantasy Fest’s Official Paint & Drink Party is on for Thurs. Oct. 26 at Sunset Green (more on that below)

1. Bahama Village Goombay Festival - Fri. Oct. 20 - Sat. Oct. 21

The Bahama Village family-friendly street party features island arts and crafts, food, and live music from noon to midnight in celebration of the diverse Caribbean history and influence on the island.

2. Royal Coronation - Fri. Oct. 20

Cast your vote for the King and Queen of Fantasy Fest at this two-hour stage show which includes a seated multi-course dinner and live entertainment. This year the event will be held at the Coffee Butler Amphitheater. The show starts at 7 p.m. Reserve your tickets in advance.


3. Prohibition Pool Party - Sat. Oct. 21

Fantasy Fest is coming to New Town! Just steps from 24 North Hotel, the specialty rum and rum cocktail bar Rum Row will host the Prohibition Pool Party as part of Fantasy Fest. Dive into the Roaring 20s for a swanky bootleg pool party with bites provided by The Blind Pig food truck and tons of alcohol. Visit the poolside Rum Row lounge from 12 to 4 p.m., located next door at our sister hotel, The Gates Hotel.

4. Zombie Zone - Red Carpet Event - Sun. Oct. 22

Also at The Gates Hotel, Zombie Zone invites all Zombie Bike Ride cyclists, spectators, and undead lovers alike to a special preamble to the big event (more on that just below). The free red carpet event summons all riders to show off their zombie costumes and dance with the dead! From 12 - 6 p.m., pull up to The Gates Hotel for free bike parking, live music, and food and drink specials.

5. Zombie Bike Ride - Sun. Oct. 22

Ride or die at this family-friendly event. Costumed bike riders leave Fort East Martello at 6 p.m. and head down A1A for the free after-party at the Coffee Butler Amphitheater.

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6. Heroes and Villains Run/Walk 5K - Mon. Oct. 23

Dress as your favorite superhero or supervillain (or just come to see the costumes) at the annual Heroes and Villains Run/Walk 5K. The race winds through Old Town. Register in advance and be sure to join your fellow caped contenders for the all-you-can-eat Hog Roast afterparty. The race starts at 6 p.m. behind the Southernmost Beach Café. Afterwards, visit Sloppy Joe’s for their annual Comic Book Cape-ers Party for dancing, DJs, and a costume contest.

7. Kinky Carnival - Mon. Oct. 23

For those who dare, the 26th annual costumed adults-only Kink Party features interactive BDSM stations, fetish rooms, bondage, and more. 

8. Capt. Tony’s Party in Plaid - Tues. Oct. 24 

Dress in your favorite criss-crossing print for Capt. Tony’s annual Party in Plaid. The party will have live music, cold drinks, and plenty of people bedecked in their best plaid outfit. The party starts at 8 p.m.

9. Southernmost Scavenger Hunt and Bar Crawl - Wed. Oct 25

Gather your scavenger hunt team and visit Key West’s most popular watering holes. You’ll follow creative clues, solve riddles, and get tons of perks along the way. Plus there are prizes for the top teams. Get your tickets ahead of time and may the best team win. The bar crawl begins at 2:30 p.m. Can’t make it on Wednesday? There are other crawls scheduled for Thurs. Oct. 26 and Sat. Oct. 28.

[5 Tips for Surviving Fantasy Fest]

10. Pet Masquerade - Wed. Oct. 25

This year’s masquerade will be extra special, as the event’s emcee, owner, and promoter is retiring and has asked that the 2023 masquerade be the biggest one in the books. A carousel of costumed pets and their human companions take the stage at the Coffee Butler Amphitheater for a delightful show for all ages.

11. Wharfstock - Wed. Oct. 25

Travel back to the 60s with Schooner Wharf, where it’s all things tie-dye, flower power, peace, and love at this groovy gathering. Dress in your best hippie outfit for a chance to win prizes. Wharfstock begins at 7 p.m.


12. Rock On With Your Smock On: Fantasy Fest’s Official Paint & Drink Party - Thurs. Oct. 26

The exciting and fun-filled art class at 24 North Hotel’s Sunset Green includes all the art, supplies, and instruction you need to create your own masterpiece. Artistic experience is not required and everyone is welcome! Reservations to Fantasy Fest’s Official Paint & Drink Party are required.

13. Sloppy Joe’s 44th Annual Toga Party - Thurs. Oct. 26

The “original Fantasy Fest event” will have live music, dancing, and a house DJ. Don a traditional ancient toga or create your own using the Fantasy Fest theme “Uniforms & Unicorns.” Festivities begin at 8:15 p.m. Stick around for the Toga Ceremony and a chance to win prizes.

14. 40th Annual Headdress Ball - Thurs. Oct. 26

The premier LGBTQ+ event of Fantasy Fest sees competitors vie for the $3,000 prize for best headdress at the Coffee Butler Amphitheater. The 8 p.m. show also features several acts, bar and food service, and Aqua’s Laurie Thibaud as host. Make sure to get your tickets ahead of time.

15. Fantasy Market - Fri. Oct. 27

Food vendors, arts and crafts, food and libations, and “costumed frivolity” abound at the Truman Waterfront Park from 10 - 3 p.m. Don’t miss your chance to shop and support local.

16. Fantasy Fest Parade - Sat., Oct. 28

Join 75,000 costumed (or just barely dressed) partygoers for the parade of the year down Duval Street. The parade starts at 7 p.m. before snaking through Old Town. Participants go all-out in hopes of winning prizes.


Now all you have to do is put this information to good use with a trip to Key West, where summer never ends. 24 North Hotel has a low-key vibe and offers shuttle service to Old Town. An on-site Starbucks, awesome pool area, and other amenities makes 24 North Hotel your best choice for Fantasy Fest. Check out our special offers here and don’t forget to secure your spot for Rock on With Your Smock On: Fantasy Fest’s Official Paint & Drink Party on Thurs. Oct. 26 at Sunset Green.

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