Event Dates
From: Thursday, October 23, 2025
To: Thursday, October 23, 2025
The Key West
Annual Headdress Ball 2025
The premier gay and lesbian event of the Fantasy Fest celebration proudly returns with an epic night of costumes and prizes.
The Key West Annual Headdress Ball 2025
The Key West Headdress Ball is the premier gay and lesbian event of the Fantasy Fest celebration.
- Visiting for the event? If you are looking for a last minute deal or want a larger hotel with great amenities, check out the Key West Marriott Beachside. Alternatively try Alexander’s Guesthouse for a unique gay escape.
The Competition
- This unusual competition allows contestants to go “head to head” to impress the audience with what they’ve got from the shoulders up!
- Over twenty five contestants will parade their Headdress creations to vie for the $3,000 first prize.
The 2025 Annual Headdress Ball
- Next edition – Thursday 23rd October, 2025.
- The ball begins at 8 PM. The event is held at the Coffee Butler amphitheater at Truman Waterfront Park, a 4 minute drive from the bars along Duval street.
- First Place prize is $3,000; Second Place is $1000, and Third Place is $ 500 for the best Headdresses, judged from the shoulders up.
- La Te Da’s Randy Roberts opens the show and Laurie Thibaud of Aqua Idol Fame returns as the Emcee. WEOW’s Rudegirl oversees the music.
- Proceeds from the Headdress Ball go to promote LBGTQ+ Tourism to Key West. Following the show there will be a special Happy Hour Disco Dance at the Aqua Sidebar.
History of the event
- Over three decades ago a group of Key West business people gathered together to form the Key West Business Guild, the nation’s oldest LGBT Chamber of Commerce.
- Only a few years later during the fledgling years of Fantasy Fest, that same group started the Headdress Ball. The Ball served then, as it does now, as a major fundraiser for the Guild.
Gay Key West – Where to stay?
Most of the gay bars in town are clustered along colourful Duval Street. Check out our Gay Guide to Key West.
The following hotels are close to the gay bars and beaches:
Duval Gardens, Truman Hotel, The Gardens Hotel, Paradise Inn
Recommended Hotels
Where to stay close to all the gay bars
Our top 4 selections with the best rates.
Where we stay!
The Paradise Inn is our favourite place to
stay in Key West. Great location & service
Official Website
For further information and advice on
The Headdress Ball, visit The Website
Gay Map of Key West
Most of the gay bars in town are clustered along colorful Duval Street, in the historic district, which is also home to dozens of fun shops and inviting restaurants.
526, Angela Street, Key West, Monroe County, Florida, 33040
This adult-only hotel offers two outdoor pools. Duval Street is a 1-minute walk away, and Key West Butterfly and Nature Conservatory is 3 minutes’ drive from the hotel. A private balcony or patio with property views is provided in all rooms at The Gardens Hotel Key West. A flat-screen cable TV, ironing facilities, and a refrigerator
Douglas House, 419, Amelia Street, Key West, Monroe County, Florida, 33040
Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool. Free Wi-Fi is also available. A microwave, refrigerator and coffee-making facilities come standard in each room
819 Simonton StreetKey West, FL 33040
Paradise Inn - Adult Exclusive is located in Key West and features landscaped grounds with brick paths and a lotus pond with koi and tropical turtles. A complimentary continental breakfast is served in the lobby.
611 Truman AveKey West, FL 33040
This trendy Key West boutique hotel features an outdoor pool and modern rooms equipped with iPod docking stations and flat-screen TVs. South Beach - Key West is 0.8 km away from the property.
1 Duval St, Key West, FL 33040
Featuring air-conditioned accommodation with a private pool, 3 bedrooms, a TV with cable channels, an equipped kitchen with a dishwasher and a microwave, a washing machine, and 4 bathrooms with a shower.
Key West, Florida 33040
This Air conditioned holiday home includes a living room with a TV with satellite channels, a kitchen with a dishwasher and an oven, as well as a coffee machine and a washing machine. A Swimming pool & Free WiFi
Key West, Florida 33040
This Air conditioned holiday home has a living room with satellite TV, a fully equipped kitchen with an oven and a microwave, 2 bedrooms and a bathroom with shower. A swimming pool and a Barbecue. Free WiFi
Key West, Florida 33040
The holiday home includes a Living room with TV, a kitchen with a dishwasher and a coffee machine. There is a bathroom with a shower and hairdryer. A Private swimming pool and a barbecue. Free WiFi
724 Duval Street, Key West, FL 33040
The Bourbon St. Pub has been known world over for its Hot Men and Boys. And you can catch them each and every night on top of the bar for your viewing pleasure, starting at 10 PM.
The hottest men and boys come from all over the world to perform for you. Many of these hot guys want to come to the island for a vacation and while here make some extra money!
801 Duval Street Key West, FL 33040
Gay Cabaret bar, Drag shows & karaoke very popular and always busy
711 Duval Street Key West, FL 33040
Gay Night club and bar with Drag shows
801 Duval Street Key West, FL 33040Gay
Gay Male Leather & Levi Bar -with a Back Room. Everyone is welcome!
1125 Duval Street Key West, FL 330403
La Te Da, a Key West landmark with a piano bar, terrace bar, and cabaret. The best live entertainment on the island!
900 Simonton Street Key West, FL 33040Fun
Happy Hour noon till 8pm daily. Karaoke nightly from 9:30 with pool table
Recommended Hotels in Key West By Booking
Book with confidence. Get the best Prices from our partner Booking.com
We have chosen hotels in Key West that keep you close to all the shops, restaurants, bars & fun
The Gardens Hotel
4 Star, adults-only
- 4 Star, Adults-Only with Two Outdoor Pools
- Close to the gay district
- Balcony or patio, flat-screen TV
- Adults-only, two pools, one-minute walk from Duval Street, rooms with balconies or patios.
Paradise Inn
3 Star, Adult Only
- 3 Star, Landscaped Grounds with Koi Pond
- Close to the gay district
- Sitting area, cable TV, microwave
- Adults-only, landscaped grounds, complimentary breakfast, suites with sitting areas and kitchen.
Douglas House
3 Star, Adult Only
- 3 Star, Near Ernest Hemingway Home
- Close to the gay district
- Microwave, refrigerator, free Wi-Fi
- Adults-only, minutes from Ernest Hemingway Home, offers free parking, pool, & microwaves.
Truman Hotel 3 Star
Trendy Boutique
- 3 Star, Trendy Boutique with Outdoor Pool
- Close to the gay district
- iPod dock, flat-screen TV
- Trendy boutique hotel, outdoor pool, modern rooms with iPod docking stations, and refrigerators.
Video of The Key West Annual Headdress Ball
Highlights Headdress Ball” In Key West
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