It’s October in Key West, and you can feel the excitement in the air as our island gears up for its annual Fantasy Fest celebration. The 10-day festival will be commemorating its 40th anniversary with world-famous costume contests, action-packed street festivals, adult-themed revelries and a dazzling grand parade.

Monopoly Headdress Ball Key West

Jay Solley is attired as “Mr. Monopoly” at the 2018 Fantasy Fest Headdress Ball in Key West. (Photo by Rob O’Neal, Florida Keys News Bureau)

It is definitely one of the largest and most popular events held in Key West, and boy do we have a lot of parties! Fantasy Fest organizers announce a different theme each year, providing a new creative challenge for merrymakers to design costumes and floats that transform our island into a veritable fantasyland.

Fantasy Fest 2019 takes place Oct. 18-27 and this year’s theme is “In Tune But … Off Key.” The zany musical concept is sure to inspire some incredible costuming.

The festival highlight is a spectacular parade through Key West’s historic Old Town — this year scheduled Saturday, Oct. 26. The procession of floats is extravagant, glitzy and entertaining with its elaborately costumed riders tossing beads to the spectators lining the streets.

With 10 full days of festivities, you may find yourself a bit overwhelmed when trying to decide which events you should attend. Well, have no fear — Greg is chiming in with six must-do parties and activities held at some favorite LGBTQ hangouts.

The Rocky Horror Show. The live cult classic performance, starring renowned female impersonator Christopher Peterson and a local cast of hilarious actors, will be staged Oct. 19-25 at 7 p.m. at the Waterfront Playhouse, located at 407 Wall St. Participation bags will be on sale at the venue. Tickets can be purchased by clicking here or by calling 305-294-5015.

Fantasy Fest king and queen Key West

King Larry and Queen Bernadette reigned over the 2018 Fantasy Fest celebration. (Photo by Peter Arnow)

Royal Coronation Ball. The Royal Campaign comes to a close Friday, Oct. 18, when the royal hopefuls who raise the most funds for A.H. of Monroe County are crowned king and queen of Fantasy Fest. The coronation includes a two-hour show and dinner, with fabulous entertainment by local celebs and the candidates at Key West’s Truman Waterfront Park Amphitheater. Click here for tickets or call 305-295-9112.

The 37th Annual Headdress Ball. The show features more than 20 extraordinarily creative entrants and nonstop entertainment that never disappoints the appreciative crowds. Wearing lavish masks and innovative headgear creations — many with extravagant designs featuring feathers, sequins, exotic decorations or even mechanical elements — they compete for awards including a grand prize of $3,000. The extravaganza is held Thursday, Oct. 24, at the amphitheater at Truman Waterfront Park. General entry begins at $30 per person, with reserved tables for four people starting at $250. Click here for tickets.

Bourbon St. Pub’s Tea in the Street and Pool Party. Get ready for one of Fantasy Fest’s premier afternoon dance parties with DJs, drag queens, and lots of libations Friday, Oct. 25, on Duval Street. Then make your way to the New Orleans House (located at 724 Duval St.) for an epic “Splash” pool party from noon to 5 p.m. Entrance to the venue is free with food and drinks for purchase.

Fantasy Fest parade Key West

The festival highlight, featuring large elaborate floats and marching groups, is the Bud Light Fantasy Fest Parade. (Photo by Andy Newman, Florida Keys News Bureau)

Glitter and Glow Party Presented by Brown Sugar Bourbon. Do you prefer an evening soiree? Then get your glitter on and your dancing shoes ready for a night of amazing music and cocktails Friday, Oct. 25. Partygoers will be glowing from 8 p.m. to 4 a.m. at the Sidebar Key West, located at 504 Angela St. There will also be a contest for the best glitter and glow “getups.”

Bourbon St. Pub’s VIP Parade Balcony Bash. This is THE PLACE to be when watching the Bud Light Fantasy Fest Parade Saturday night, Oct. 26. The viewpoint from the balcony of the New Orleans House is phenomenal. A $200 ticket includes a catered buffet and top-shelf open bar. Be sure to reserve your tickets ASAP as balcony viewing sells out quickly. Click here for tickets or call 305-293-9800.

Want more information about Fantasy Fest’s dozens of incredible events? Explore the festive offerings here.

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