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Fantasy Fest 2025: Where “Bedtime Stories & Magical Monsters” Come to Life

February 22, 2025 • KW Concierge

Key West, Florida, never shies away from a good party. But every October, the island truly pulls out all the stops for Fantasy Fest, a 10-day celebration of creativity, community, and costumes galore. This year’s theme, “Bedtime Stories & Magical Monsters,” invites revelers to bring their wildest childhood dreams—and nightmares—to life. If you’re looking for a festival that transforms an entire tropical town into a nonstop masquerade parade, look no further. Fantasy Fest is the place to swap your everyday clothes for enchanting outfits, dance in the streets to the pulsing beat of live music, and make unforgettable memories under the Key West sun.

A Brief History of Unbridled Imagination

Fantasy Fest may now be world famous, but it began in 1979 as a local solution to a very real problem: how to lure visitors to Key West during the sleepy shoulder season. With October hotel rooms empty and shops boarding up, a few visionary business owners decided a festive Halloween-themed parade and costuming party might just do the trick. They were absolutely right. Over the decades, that original “small but outrageous” parade has flourished into a 10-day extravaganza, attracting as many as 75,000 visitors each year.

The festival’s party-forward atmosphere celebrates the quirkiness that Key West is known for. Since day one, organizers have encouraged imaginative participation, whether through over-the-top ensembles, body paint artistry, or decked-out parade floats. Even more meaningful is the positive community impact: the event has generated millions of dollars for local nonprofits through various fundraisers, such as the iconic campaign for the King and Queen of Fantasy Fest, which for 30 years raised funds for A.H. Monroe and now supports The Florida Keys SPCA.

Why Travelers Love Fantasy Fest

1. Endless Creativity: From whimsical fairies to fearsome beasts, Fantasy Fest’s theme invites you to become someone—or something—else entirely.
2. Day-to-Night Revelry: The schedule is packed with street fairs, pool parties, costume contests, and late-night galas. There’s always something fun on tap.
3. Island Vibe Meets Halloween Spirit: Picture a tropical twist on classic Halloween flair, set against pastel conch houses and swaying palms.
4. Community Camaraderie: Locals love their festival as much as tourists, so you’ll find yourself instantly welcomed—and maybe even roped into a makeshift conga line on Duval Street.
5. Unforgettable Parade: The can’t-miss finale is the grand Fantasy Fest Parade, an explosion of color, music, and spirit that weaves from the Gulf of Mexico to the Atlantic Ocean.

Must-See Events: Mark Your Calendar

Below is a taste of the 10-day schedule, spotlighting standout events that will help you plan your perfect Fantasy Fest experience.

  1. Bahama Village Goombay Festival

    1. When: Friday, Oct. 17 & Saturday, Oct. 18
    2. What to Expect: A lively, family-friendly street party celebrating island heritage in historic Bahama Village. Enjoy non-stop reggae and soca beats on the main stage, browse local arts and crafts, and savor tropical treats.

  2. Royal Coronation

    1. When: Friday, Oct. 17
    2. Where: Key West’s Coffee Butler Amphitheater
    3. Why Go: Witness the crowning of the King and Queen of Fantasy Fest—candidates who raise funds for The Florida Keys SPCA. This two-hour stage show brims with local talent, flamboyant performances, and a philanthropic spirit.

  3. Zombie Bike Ride

    1. When: Sunday, Oct. 19
    2. Spooky Cyclists: Thousands of costumed “zombies” ride from Fort East Martello down A1A, culminating in a free dance party. It’s kid-friendly early, then gets wild as the evening progresses.

  4. Tutu Tuesday

    1. When: Tuesday, Oct. 21
    2. Twirling in Tutus: Don your most whimsical tutu and dance your way through Key West’s best bars. There’s even a Tutu Tuesday Pre-Party Parade!

  5. Key West Pet Masquerade

    1. When: Wednesday, Oct. 22
    2. Where: Key West Amphitheater
    3. Fur-tastic Fun: Cuteness overload as costumed pets and their owners strut their stuff. From miniature mermaids to dapper dachshunds, you never know what creative combos will grace the stage.

  6. Sloppy Joe’s Toga Party

    1. When: Thursday, Oct. 23
    2. Roman Holiday: Wrap up in your best bedsheet and live like a Greek god or goddess for the night. A high-energy costume contest and live music keep the festivities rolling.

  7. Headdress Ball

    1. When: Thursday, Oct. 23
    2. Where: Coffee Butler Amphitheater
    3. Highlights: Fabulous headpieces take center stage at Fantasy Fest’s premier LGBTQ+ event. Designers compete for top prizes, and the show’s proceeds support the Key West Business Guild. Expect jaw-dropping creations and show-stopping entertainment.

  8. Captain Morgan Masquerade March

    1. When: Friday, Oct. 24
    2. Route: Starts at Old Town Wine & Spirits on Truman Avenue (plus a second starting point at Island House/Alexander’s Guesthouse), meanders through Old Town, and ends on Duval Street.
    3. Local’s Tip: Often called “the Locals’ Parade,” this lively march invites everyone to join in, costume up, and roam from guesthouse to guesthouse for surprise refreshments.

  9. Key West Fantasy Fest Parade

    1. When: Saturday, Oct. 25, 7 PM
    2. Big Finish: Floats, dancing groups, bicycles-turned-art installations—this is the culminating event that draws tens of thousands of spectators. Don’t forget to look for the live music awards, flamboyant costumes, and confetti cannons lighting up Duval Street.

Insider Tips for a Seamless Celebration

  • Plan Ahead: Lodging sells out quickly. If you can’t find a place on the island, check options in the Lower Keys.
  • Pack a Costume (or Three): One for the parade, one for a themed party, and one just in case. You’ll thank us later.
  • Stay Hydrated and Protected: Even in October, Key West can be hot and sunny. Drink water, wear sunscreen, and mind your “party pace.”
  • Support Local Charities: Many events double as fundraisers—your entry fees could help the local SPCA or a community health clinic.

Ready to Make Magic Happen?

Whether you’re coming for the outlandish costumes, the incredible parade, or just to let loose in paradise, Fantasy Fest 2025 promises to be one for the ages. Join us in Key West to discover why grown-ups love playing dress-up just as much as kids do—especially when there’s a full island of fun waiting to cheer them on. Pack your suitcase (don’t forget your wings, capes, and crowns!) and head to the southernmost spot in the continental U.S. for a vacation you’ll be talking about all year. Let your creativity run wild, channel your favorite bedtime legends and magical monsters, and come see why Fantasy Fest truly is the can’t-miss party in paradise. We’ll save you a spot on Duval Street—just follow the confetti trail!