Event Dates
From: Thursday, October 26, 2023
To: Thursday, October 26, 2023
The Key West
Annual Headdress Ball 2023
The premier gay and lesbian event of the Fantasy Fest celebration proudly returns
The Key West Annual Headdress Ball 2023
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 2023 Annual Headdress Ball
- 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.
- Eight great talent acts by Key West performers will also be featured. Laurie Thibaud of Aqua Idol fame, will be the emcee. Christopher Peterson opens the show and there will be a special act by the Aquanettes. Bar service during the performance.
- 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
- 2023 Venue to be confirmed
- 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 currently trending with our readers. All 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.
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
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
Paradise Inn
3 Star, Adult Only
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. The suites at Paradise Inn – Adult Exclusive include a sitting area with cable TV. A microwave, refrigerator, and coffee facilities
Douglas House
3 Star, Adult Only
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
Truman Hotel 3 Star
Trendy Boutique
This trendy Key West boutique hotel features an outdoor pool and modern rooms equipped with iPod docking stations and flat-screen TVs. All rooms at the Truman Hotel are equipped with a refrigerator. Each room is styled with wood floors, and bathrooms boast tiled showers and marble vanities.
Video of The Key West Annual Headdress Ball
Highlights Headdress Ball” In Key West
Recommended Hotels in Key West BY Expedia
Book with confidence. Get the best Prices from our partner Expedia
We have chosen hotels in Key West that keep you close to all the shops, restaurants, bars & fun
Hyatt Centric
4 Star, Great Pool
At Hyatt Centric Key West Resort and Spa, hit the nearby beach, relax by an outdoor pool, or spend the day at a marina. All 120 soundproofed rooms feature iPod docks and room service. Guests will appreciate conveniences like sitting areas and coffee makers, while flat-screen TVs with satellite channels
Ocean Key Resort
4 Star, Stylish
2 restaurants, a full-service spa, and an outdoor pool are available at this smoke-free resort. WiFi in public areas is free. Other amenities include 3 bars/lounges, a poolside bar, and valet parking. All 100 individually decorated rooms feature free WiFi and iPod docks. For a bit of entertainment, guests will find LCD TVs with satellite channels
The Cabana Inn
3 Star, Readers Choice
An outdoor pool, a snack bar/deli, and a spa tub are available at this guesthouse. Other amenities include self parking, coffee/tea in a common area, and a business center. All rooms are individually decorated and offer free bottled water and ceiling fans. For a bit of entertainment, flat-screen TVs come with cable channels
The Saint Hotel
3 Star, Modern Classic
Along with a restaurant, this smoke-free hotel has an outdoor pool and a 24-hour fitness center. WiFi in public areas is free. Other amenities include a bar/lounge, a rooftop terrace, and valet parking. All 36 individually decorated rooms provide free WiFi, free wired Internet, and iPod docks. LCD TVs with digital channels
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