Fantasy Fest

Fantasy Fest

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Date
Thu, Oct 1

From publicly posted calendar Checked yesterday

About this event

On Daisy

One of 14 upcoming events at Winslow's Bungalows - Key West Historic Inns.

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From Winslow's Bungalows - Key West Historic Inns

Fantasy Fest is Key West at its most uninhibited, a ten-day celebration of creativity, self-expression, and pure island energy. Each year, the streets transform into a vibrant spectacle of elaborate costumes, dazzling body art, themed parties, and unforgettable parades. From daytime poolside gatherings to late-night revelry along Duval Street, the festival invites you to step into a world where imagination runs wild and anything feels possible. Whether you come to people-watch or fully embrace the fantasy, there’s no experience quite like it. Signature events like the grand parade and themed costume contests bring together locals and visitors alike in a playful, electric atmosphere. It’s bold, colorful, and unapologetically fun—making Fantasy Fest one of Key West’s most iconic and talked-about celebrations. Festival officially begins with themed parties and events across Key West Goombay Festival (Caribbean street fair vibes + food + music) Zombie Bike Ride – one of the most iconic, high-energy early events Learn more: View Full Fantasy Fest Schedule Tutu Tuesday & themed costume nights Pet Masquerade (fun + slightly more casual crowd) Headdress Ball – one of the most artistic, over-the-top costume showcases Learn more: Explore Events & Parties Known as the “locals’ parade” Walking party through Old Town with costumes, drinks, and live energy Less crowded than Saturday, but still electric Learn more: Masquerade March Details The main event of the entire festival Massive floats, costumes, performers down Duval Street Draws tens of thousands of spectators every year Learn more: Fantasy Fest Parade Info “The Fat Lady Sings” Tea Dance (closing celebration) Pool parties + recovery vibes across the island Learn more: Festival FAQs & Closing Events Think pink and join us for Flocktail Fridays at Isabel's Lighthouse. Wear your favorite pink attire, tag @KeyWestHistoricInns in your social post, and receive 10% off your bar tab from open to close. The Studios of Key West is a historic Old Town arts center offering sunset rooftop happy hours, rotating art exhibitions, performances, film screenings, workshops, and unique spaces for meetings and events bringing together local and visitors in an inspired island setting. Classic, delightful lemonade with a twist! Gather around the retro bar cart in our lobby daily for a crisp lemonade and a floater of locally-made Wreckers Vodka by Key West Trading Co. at The Fitch Lodge. Join us each afternoon at Ella's Cottages for a complimentary glass of Roseblood Rosé, offered daily from 3:00 PM to 4:00 PM.

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