Key West Fantasy Fest 2026

Fantasy Fest Key West 2026

Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked.

• Stay at the H2O Suites- Adults Only, 200 m from Duval Street rated “Superb” by guests and featuring a year-round outdoor rooftop pool with a sun terrace. 

Fantasy Fest

• Next Edition: Friday 16th October – Sunday 25th October, 2026.
• Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!

Masquerade March

• Friday 23rd October 2026 – Don’t miss the Masquerade March (Locals’ Parade), steps-off 5:30pm. The route threads through Old Town and feeds into the Duval Street action; it’s walk-along, not fenced.
• Step-off is 5:30pm Friday; two start points: Fleming & White St and the 700 block of Frances St. Line-up from 4pm if you want to be near the front.
• Guesthouses on the route offer complimentary drinks until they’re gone; bring a reusable cup and a photo ID.
• Pose for some insta-worthy snaps  around Island House and Alexander’s Guesthouse, known as “Paparazzi Row”.

Grand Parade

• Saturday 24th October 2026 – Grand Parade:  7pm. Runs the length of Duval Street from the Gulf end toward the Atlantic.
• Crowds pack Lower Duval (north end, near the Gulf). Upper Duval and the Whitehead/Angela area are calmer if you want space and easier movement. Arrive 60–90 mins early for curbside.
• Ticketed balcony parties sell out fast and solve the crowd issue: New Orleans House “VIP Balcony Bash” (Bourbon St Pub complex, 724 Duval): open bar, buffet, private restrooms, bead toss, 6pm doors; 7–10pm.
• 801 Bourbon has hosted “largest balcony on Duval” parties for the past several years.
• Mangoes promotes an elevated patio view each year.
• For parade views, stay at Ocean Key Resort & Spa, at the parade’s Gulf end; many balconies have views of the event.

The Street Fair

• Friday 23rd and Saturday 24th October 2026 – Enjoy a two-day open-air market lining Duval Street with local art, costumes, food stalls, and nonstop live entertainment from noon through evening.

Fantasy Fest Pool Parties

• There are hundreds of events taking place during the 10 days of Fantasy Fest. Popular pool parties are held at The Equator Resort (Naked Pool Party), Alexander’s Guesthouse and The Bourbon Street Pub.
• Here’s our shortlist of what to do during Fantasy Fest 2025. The gay hotels sell out months in advance in Key West.
• If you are looking for a last minute deal or want a larger hotel with great amenities, check out the Key West Marriott Beachside.

The Headdress Ball

• Typically Thursday – Headdress Ball Key West’s signature LGBTQ+ gala, blending elaborate costumes, drag performances, and a runway competition under the stars.
• Held at the Coffee Butler Amphitheater, the charity event takes place in the early evening and is a must-do event during the 10 days of celebrations and parties.

Gay Highlights

There are hundreds of different parties and events throughout the two weekends of Fantasy Fest. Remember, parties are not just for gay visitors, however the biggest and best events kick off from the second weekend, starting on Sunday. Here’s our top picks for gay visitors:

• Zombie Bike Ride 🚴‍♂️💀: Join the undead cyclist parade on Sunday! Whether you’re a bike pro or just here for fun, don’t miss it. Afterparty? Head to Bourbon Street Bar.
• Underwear Party 🩲🎉: Monday at Bourbon Street Pub. Wear as much (or as little) as you like. Gents only.
• Tutu Tuesday 🩰🎈: Wear a tutu, parade around the island, and party at 22&Co. Tutu required for entry. Go wild.
• Desire Male Fetish Party 🖤🔥: Wednesday’s spicy event at New Orleans House. Watch or dive into the fun.
• Exposed Party 🎵💦: Thursday’s wild night at Bourbon Street Pub. Pool, foam, music, and more. Dress code? You decide!
• Masquerade Parade 🌈👽: Friday’s Masquerade March. Start at Key West Cemetery and drink along the way, ending at Equator Resort.
• Fantasy Fest Parade 🎭🥳: Saturday’s grand parade on Duval Street. Think of it as a Super Bowl of parties.
• Tea Dance 💃🍹: Sunday’s chill party at La Te Da. Show your style, wear sunscreen, and enjoy.
• Survival Tips 📝: Costumes are key and “too risqué” isn’t a thing.

Popular Venues during Fantasy Fest

• Bourbon Street Pub: Dance floors, drag shows, and dreamy go-go boys. Perfect for a night of non-stop fun and don’s miss the VIP Balcony Bash.
• 801 Bourbon Bar: Two words: Drag Cabaret. You’ll be laughing and singing along before you know it. Late bar till 4 am.
• La Te Da: A classy spot for cocktails, cabaret, and candid conversations. Don’t miss the “Fat Lady Sings”, Final T Dance onn Sunday 25th October, 2026, from 4 pm to 8 pm.
• The Saloon: A mix of leather vibes with a tropical twist. Dive in for some daring fun.
• Aquaplex Key West: Glamour meets groove. Enjoy dazzling drag shows and dance the night away. Don’s miss the Aquanettes drag shows; comprises of Aqua, 22&Co and Back Bar, running Fantasy Fest programming all week.

Where to stay during Fantasy Fest

Most of the gay bars in town are clustered along colourful Duval Street. Check out our insider gay guide to Key West

Here are the Hotels we recommend that keep you close to all the action

Duval Gardens,    Truman Hotel,    The Gardens Hotel,    Paradise Inn