HISTORIC WONDERS OF THE WEST

Ten locations and events that had a significant impact on Key West’s rich LGBTQ history.

1. DUVAL STREET

The epicenter of the city’s arts and gay culture, Key West’s main drag is home to some of the city’s most iconic establishments, from nightclubs to museums, guesthouses to gardens. It is also the location of longstanding institutions Captain Tony’s Bar (est. 1970), Sloppy Joe’s (est. 1933), and the oldest bar in Key West, Green Parrot Bar (est. 1890).

2. TENNESSEE WILLIAMS MUSEUM

The house that playwright Tennessee Williams lived in the little yellow house at 1431 Duncan Street from 1948 until his death in 1983. His beloved home has been converted to a museum honoring his life and literary achievements.

due to its proximity to the Navy base front gates, and Jack Gray’s Rum Runner Room (later Delmonico’s Bar), all of which had a large shrimper and servicemen clientele.

Meanwhile, the allure of the tranquil island life as an escape from the fast-paced hectic mainland life attracted authors, playwrights, composers and their ilk. The rst was composer and conductor Leonard Bernstein, best known for his iconic musical, West Side Story. He rst visited Key West in 1941, and wrote his rst published opus, Sonata for Clarinet and Piano, during his stay. He would later write a ballet, Conch Town, as a salute to Key West natives. Author and playwright Tennessee Williams arrived in Key West in 1948 and spent the last 34 years of his life there. Many of Williams’ world-renown plays such as The Rose Tattoo and Night of the Iguana were written in Key West. Both world-famous openly gay men were instrumental in drawing national and international attention to Key West.

The city’s lively gay and artist mecca status lasted until early 1970. Then Old Town became quiet. “The town was one of the last bastions of ‘hippiedom’ after a large part of the Navy pulled out” wrote Ross. The closure of the naval base caused a population of 45,000 to drop to 15,000 seemingly overnight. “Most of the buildings, especially downtown, were old, weathered and dilapidated,” wrote Ross. “You could see the potential of these old conch homes and buildings, but no one at the time seemed to be interested in doing any renovation.”

Cori Convertito, PhD, the curator of the Key West Art & Historical Society, said in her presentation, “Florida Keys or Bust: A History of Tourism” that the closure of the naval base had a domino e ect. Businesses could not sustain themselves from a drop of population from 45,000 to 15,000 so they shuttered. Tourists stopped coming because the businesses were closed. With tourism at a halt, hotels and restaurants closed.

“There was a large portion of South Florida who were gay and saw an opportunity to move to the keys, speci cally Key West, buy the property pretty cheap and x it up,” said Convertito. “What they did is create the next wave of tourism for all of us.”

The Second Wave

Ricki Fessler lived in Coconut Grove, Fla. in the mid-70s where he worked as a bartender. He met a Norwegian patron named Sven Christensen whom he learned owned The Monster on Fire Island, NY. Christensen saw something in Fessler. He asked him if he would be interested in helping him open a gay bar in Key West.

“I said, well, I don’t know. It doesn’t seem very gay to me,” said Fessler. At the time, Key West was mainly populated by shrimpers and Navy men. “He said you only have to do it for six weeks.”

Fessler was instantly attracted to the offer. Then he was hooked by the beauty of Key West, and the appeal of The Monster he helped open there. “It became an instant hit. All of a sudden, people started coming down because [Christensen] owned the one on Fire Island,” said Fessler. The Monster on Key West was considered Studio 54 South.

“Tennessee Williams and Truman Capote used to sit at the end of the bar at happy hour,” added Fessler. “Tennessee drank his whiskey and Truman sipped white wine while they did poppers.”

Drag queen phenomena Divine was a dear friend of Fessler and former roommate in New York City brie y. Divine lived in Key West for a short time. One of the most memorable and still talked about drag performances was the one given by Divine

Queering The Way

South Florida is far from the only place to feel the impact of LGBTQ+ tourism. In his book, The Queering of the Redneck Riviera, Jerry T. Watkins III focuses on the Florida panhandle, depicting the complex history of how its growing LGBTQ+ population overcame the reactionary push for “family-friendly” environments and turned the Redneck Riviera into the Gay Riviera. The book is part of a growing body of research on how LGBTQ+ presence changes the cultural fabric of cities, often leading to economic growth.

at The Monster when she came down from New York and performed her Disco hit, You Think You’re a Man.

Politicians frequented The Monster too. “Senator John Spottswood and his wife used to come into The Monster quite a bit,” said Fessler. “I had been working there for a couple of years and [Mrs. Spottswood] came in one night and asked me, ‘Ricki, do you like living here? Do you think you want to stay here?’ I said, yeah. And she said, ‘I have three words for you.’ And I said, ‘what’s that Mary?’ And she said, ‘buy real estate.’ However, at the time I was more interested in getting Quaaludes and martinis.”

Other gay and lesbian business people had the same thought regarding real estate. It started at Zero Duval Street with the construction of the Pier House—the island’s rst high-end, all-inclusive resort. It was built by gay local Key Wester David Wolkowsky, a marketing whiz who invited travel journalists and publicists from all over the world to stay at the Pier House and experience Key West’s beauty and allure. Local media aptly called Wolkowsky “Mr. Key West” and the “Father of Key West Tourism.” By the middle of the 1970s, there were more than 30 same-sex guest homes that catered to gay men thanks to a consistent supply of gay tourists, including Key West’s only all-male guesthouse on Duval Street, New Orleans House. Fleming Street had four or ve highly popular gay guest houses on it, including Equator Report, Alexander House, and Island House. “We nicknamed it Flaming Street,” joked Fessler.

Soon gay-owned and gay-friendly businesses appeared everywhere. Establishments such as La Te Da, Papillion, The Mermaid Lounge, The Copa, Beach Bar at Pier House and Delmonico’s Bar on Duval Street entertained the throngs of LGBTQ and straight visitors with drag performances while gay-owned galleries and stores provided venues to shop.

The Impact

Gay merchants on the island came together in 1978 to discuss the special task of marketing to LGBTQ tourists. It was clear that gay tourists were enthusiastic, exible travelers with disposable means. As a result, the Key West Business Guild was established as the rst LGBTQ chamber of commerce and destination marketing organization in the nation.

Steve Murray-Smith, at the time, Steve Smith (1950 - 2022) was the marketing director of the Key West Business Guild and pioneered Key West as a premiere Gay Destination. Murray-Smith traveled the coun-

3. THE MONSTER

Founded by Sven Christensen and local bartender Ricki Fessler, the popular restaurant/ gay club is considered one of the catalysts for the revitalization of LGBTQ+ tourism in Key West

4. RICHARD HEYMAN

When he was elected Mayor of Key West in 1983, he became America’s first openly gay mayor.

5. ONE HUMAN FAMILY

The mantra and philosophy, created by openly gay local artist J.T. Thompson, was adopted as the o icial philosophy of Key West in 2000.

6. THE KEY WEST BUSINESS GUILD

Established in 1978, the Guild is the oldest LGBTQ chamber in the USA and one of North America’s oldest gay and lesbian destination marketing organizations.