Home » Key West — 11 Exciting LGBTQ+ Events

Key West — 11 Exciting LGBTQ+ Events

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by Our Editors
Celebrating Pride in Key West (Photo courtesy of fla-keys.com)

“There is so much to do on this little island,” says Fritzie Estimond, Associate Director at the Key West Business Guild.

Key West Pride (Photo courtesy of fla-keys.com)

Pack your bags and head to Key West to experience some of the best and most exciting LGBTQ+ events in the USA.

“There is so much to do on this little island,” says Fritzie Estimond, Associate Director at the Key West Business Guild. “Since moving here 14 years ago, I have discovered why Key West has been dubbed the gay mecca of the United States. We have so many events that cater to all demographics and I am proud to be a contributor to a portion of that, working with The Key West Business Guild to proudly host Key West Pride, Tropical Heat, Womenfest, and the Headdress Ball (which is an official event during Fantasy Fest).” As our go to person in this unique and diverse destination, Fritzie shares with us her list of 11 exciting events every LGBTQ+ visitor should experience in Key West.

KEY WEST PRIDE
Key West is legendary for its laid-back style, open, accepting atmosphere, and supportive community. Whether you’re looking to party with friends, travel with family, or get lost in the magic of our tropical island, you’ll soon understand why Key West created the island’s philosophy “One Human Family” and became one of the most integrated and unique communities in the world. Here you can celebrate Pride every day, or enjoy the parties and parade June 5 – 9. gaykeywestfl.com/pride

Fritzie Estimond (Photo courtesy of Fritzie Estimond)

Fritzie Estimond (Photo courtesy of Fritzie Estimond)

KEY WEST TROPICAL HEAT
Tropical Heat is a sizzling annual 5-day party for gay men ages 21 and up in Key West and the Florida Keys. The all-male themed festivities, pool parties, clothing-optional events, and adult-oriented entertainment promise to be HOT! August on our tropical island is always hot, but during Tropical Heat it promises to be even more so! What better way to experience Key West than by joining us for 5 days with hot guys!? August 7 – 11. gaykeywestfl.com/tropical-heat

WOMENFEST KEY WEST
For decades, Womenfest Key West has attracted thousands of lesbians, bi-sexual, queer, transwomen, and allies to what is arguably the premier LGBTQ+ vacation destination in the country. Womenfest has a simple goal: to celebrate ALL women! Key West Womenfest offers a wide range of activities for those who want to socialize, feel comfortable being themselves, soak up some sun, then party and dance the night away. Since its introduction over 20 years ago, Key West Womenfest has grown to become a standard for celebrating women ranging from all ages 21 and over. Couples, singles, and those in between are all welcome! Join us annually in September to immerse yourself in what is dubbed the HOTTEST party for women in the Florida Keys! September 4 – 8. gaykeywestfl.com/womenfest

KEY WEST HEADDRESS BALL
The Headdress Ball is the premier LGBTQ+ event of the Fantasy Fest Celebration! Contestants will take to the stage to show their headdress creations, judged from the shoulders up, and vie for the first prize of $3,000. Proceeds from the Headdress Ball go to promote Key West as a major LGBTQ+ destination worldwide. October, 2024. gaykeywestfl.com/headdress-ball

Fantasy Fest 4

Fantasy Fest 4

FANTASY FEST
Fantasy Fest welcomes a whopping 40,000 revelers for 10 days! Partake in dozens of themed costume parties, street fairs, art exhibits, live music, tea dances, and more! And don’t miss the spectacle Fantasy Fest parade along Duval Street! October 18 – 27 facebook.com/FantasyFest

QUEEN MOTHER PAGEANT
Drag queens compete for the coveted title of “Queen Mother” in this local favorite event. All proceeds from the Queen Mother Pageant goes toward Compassionate Care Hospice and One Human Family Foundations. Each drag queen showcases their humor, evening gown attire, talent, and more. The Queen Mother serves as a charitable ambassador throughout the rest of the year at Key West events. May, 2024. keywestchamber.org

BIG GAY KEY WEST
Event Organizer Ralph Gonzalez says “Big Gay Key West invites gay chubby men, their admirers/chasers, and bears to Key West, Florida to take part in a 6-day event featuring exclusive access to beautiful, luxurious, gay male clothing optional resorts: Island House, New Orleans House, and Alexander’s Guesthouse, where guests enjoy reciprocal access to all of the properties.” Nightly happy hours and rotating pool parties will be held at the above resorts and bars throughout the event. September, 2024, biggaykeywest.org

Key West Bear Weekend (Photo by Alfredo Lopez)

Key West Bear Weekend (Photo by Alfredo Lopez)

KEY WEST TEA DANCE AT LA TE DA
The infamous Key West Tea Dance at La Te Da takes place every Sunday from 4 – 6:30 P.M. Music and dancing with resident DJs Rude Girl and Molly Blue. This Key West tradition is a fun, all-welcome event for locals and visitors alike. You are encouraged to dress up, dress down or simply come as you are and enjoy the fun! lateda.com/tea-dance

BONE ISLAND BARE IT ALL
For over two centuries Key West has been historically known as Bone Island, and Bone Island Bare It All gives a whole new meaning to that name! Two weekends each year, hundreds of gay naturists and guys who like to get naked fill up Key West’s clothing-optional guesthouses and gay-friendly hotels for a weekend of naked fun in paradise. Featured events include dance parties, pool parties, shopping, dining, sailing, performances, and tours—all naked! Check your clothing and inhibitions at the doors of Key West’s famous gay daytime and nighttime establishments. July 10 – 14, and December 5 – 8,
2024. nakedkeywest.squarespace.com

KEY WEST BEAR WEEKEND
Each year, hundreds of bears and their admirers gather to soak up the sun, the booze and each other in what has become a beloved annual tradition. And for an added treat in 2024, this year’s Key West Bear Weekend will take place from October 30th through November 3rd. That’s right boys, this year’s celebration falls on Halloween! keywestbearweekend.com

New Year’s Eve Red Shoe Drop (Photo courtesy of fla-keys.com)

New Year’s Eve Red Shoe Drop (Photo courtesy of fla-keys.com)

NEW YEAR’S EVE RED SHOE DROP
This annual, one-of-a-kind, free event on Duval Street featuring international talent is the perfect way to ring in the new year with friends in Key West, Florida! Hosted by Bourbon Street Pub, the streets are filled with revelers as the featured drag queen is lowered to the ground in a giant red shoe. 10, 9, 8, 7… Happy New Year! fla-keys.com/key-west/lgbtq


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