Key West Fantasy Fest Guide: Events, Costumes & Travel Tips

It’s almost time for Key West’s annual Fantasy Fest, beginning Sunday, Oct. 28. This year’s theme, “Oh… The Games We Play!,” brings 10 days of costume contests, masquerade balls, themed parties and other lively events. The festival opens with the Royal Coronation Ball, where the king and queen are crowned, and the island celebrates its Caribbean heritage with the family-friendly Goombay street party in Bahama Village.

Key West Burlesque presents Madam DuJour’s Magical Game Show and Burlesque Experience, while costumed pets and their owners compete for prizes during the Pet Masquerade. The schedule blends family-oriented activities with adult-focused performances and nightlife.

Highlighted events include the 36th annual Headdress Ball, featuring competitors who display enormous, intricately decorated headpieces for judging and awards. Throughout the festival, visitors are encouraged to embrace fantasy roles and join themed events in full costume. Planned gatherings this year include the Ringmaster’s Pool Party, Venetian Masquerade Ball, Zombie Bike Ride and a retro beachside celebration.

The festivities culminate with the grand Bud Light Fantasy Fest Parade through downtown on Saturday, Oct. 27. The parade features costumed performers, imaginative motorized floats, eccentric marching groups and live island-style music, drawing large crowds to celebrate the festival’s final day.

Costumed revelers help kick off the Fantasy Fest Parade Saturday, Oct. 28, 2017, in Key West, Fla. The extravaganza was the highlight event of the 10-day Fantasy Fest masking and costuming festival that ends Sunday, Oct. 29. The parade, that attracted tens of thousands of partiers, occurred about seven weeks after Hurricane Irma passed through the Florida Keys.

Costumed revelers help kick off the Fantasy Fest Parade Saturday, Oct. 28, 2017, in Key West, Fla. The extravaganza was the highlight event of the 10-day Fantasy Fest masking and costuming festival. The parade, which attracted tens of thousands of partiers, took place about seven weeks after Hurricane Irma passed through the Florida Keys. (Andy Newman, Florida Keys News Bureau)