A 100-foot section of Key West’s sea-to-sea rainbow flag unfurls along Duval Street for Pride in June 2022. LARRY BLACKBURN/Keys Weekly

The door’s always open at 808 Duval St., home of the Key West Business Guild and its Gay Key West Visitors Center, just steps from the rainbow-colored crosswalks at Duval and Petronia streets.

Inside, one will typically find two of the friendliest faces in town — executive director Kevin Theriault and events coordinator Fritzie Estimond.

The guild launched in 1978 to “encourage summer tourism and support Key West’s gay community,” its website says. 

“It was the country’s first-ever LGBTQ+ destination marketing organization. From a small original membership, it today comprises nearly 500 members representing virtually every facet of the island’s business community.”

Today, the Key West Business Guild ranks among the nation’s leading gay business associations, and its marketing efforts, supported by the Florida Keys Tourism Development Council, incorporates a gay marketing specialist and an award-winning advertising campaign.

“Some people think we don’t need to market Key West as an LGBTQ destination, but that’s just not true. So many people still come to Key West specifically because they can’t be themselves back home, and find an acceptance and a comfort level that they’ve never experienced before. They’re the people we want to reach with our marketing efforts. And based on the response we get and the people we meet at our visitor center, I think we’re doing a great job,” Theriault said.

Bourbon Street Pub hosts a pool party during Tropical Heat. LARRY BLACKBURN/Keys Weekly

The guild compiles visitor information from all the people who contact their office and visit their center on Duval Street. “We ask people their ZIP code, and do visitor surveys whenever people are here for an event, so we know where people come from, how they heard about us and what they liked about Key West and what activities they enjoyed while here.”

The Key West Business Guild’s biggest annual event, not surprisingly, is the June Pride celebration that includes shows, a parade, pool parties, boat trips, museum exhibits, comedy shows, you name it. 

“Next year will be a big deal, as it’s the 20th anniversary of our Sea-to-Sea Rainbow Flag,” Theriault said. He was referring to Key West’s famous 1.25-mile long flag that covered the length of Duval Street in June 2003, sewn by an army of volunteers, unfurled from a giant truck at the gulf end of Duval Street, then marched to the Atlantic Ocean by hundreds of proud, smiling volunteers, gay and straight.

“One of the best things about Key West and the guild is that everyone gets it, when it comes to local businesses supporting and welcoming LGBT travelers,” Theriault said, adding that he doesn’t have to deal with business owners who question the value of LGBTQ travelers as both consumers and human beings. 

“Next year is the 45th anniversary of the guild itself,” Theriault said. 

This week is Womenfest in Key West, the nation’s largest gathering specifically for women — all women, Estimond emphasized while handing a Womenfest t-shirt to a straight Key West woman.

For nearly 40 years, the guild also has hosted the extravagant Headdress Ball, “the only official LGBTQ event of Fantasy Fest,” Theriault said. Of course, he added, all of the gay bars, guest houses and other businesses host their own events that week, but Headdress Ball is the only official one. It’ll be back with a vengeance this October after COVID prompted repeated cancellations.

Each summer, the guild also sponsors and coordinates Tropical Heat, a men’s gathering in the heat of the summer. 

In addition to events that put heads in beds in Key West, the Key West Business Guild works hard for its members, Theriault said.

“We offer varying levels of membership for businesses of all sizes, as well as for nonprofit organizations and even individual memberships,” he said.

Membership benefits include a free link and listing on the guild’s website and on its Key West map, which is widely distributed. The guild also offers space to members for announcements and advertisements in its newsletter and space for promotional materials at its visitor center. Additional paid advertising opportunities are available through event sponsorships and promotional materials distributed worldwide at travel shows. 

For more information about the Key West Business Guild, membership, special events or LGBT travel, visit or call 305-294-4603.

The Key West Business Guild presents Womenfest each September, including this week, Sept. 7-11. CONTRIBUTED

Womenfest Women & Works Art & Poetry

The Key West Business Guild’s WomenFest celebrates local poets and artists on Thursday, Sept. 8 from 5:30 to 7:30 p.m. at Little Room Jazz Club, 821 Duval St. 

Women & Works features readings and a pop-up exhibit by island artists and writers.

Round-robin readings will feature Key West Poetry Guild members Rosalind Brackenbury, Flower Conroy, Arida Wright, Katherine Doughty, Fran Decker, Sheri Lohr, Sarah Goodwin, Cricket Desmarais and Kai Seava Lamontagne, along with open mic offerings by men and women seeking to share their work.

The pop-up exhibit features art available for purchase by Alicia Renner, Barbara Sage, Christy Fifer, Cricket Desmarais, Fran Decker, Katherine Doughty, Liz Acar, Lucy Hawk, Lynne Bentley-Kemp, Margo Ellis, Martha Hubbard, Sandy Sun, Roberta DePiero, Susan D’Antonio, Karen Luknis, Karen Moore.The event is open to all and free of charge. Donations for the Connie Gilbert Scholarship Fund, which benefits Florida Keys women, are welcome. For information and full event schedule, visit

If you would like to have the Weekly delivered to your mailbox or inbox along with our daily news blast, please subscribe here.

Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.