Kathy Amendola’s company logo is a pink cat with pink shades, full lips and a devilish smirk encased in a pink triangle. It’s the same image found on her petal pink business cards and on the round white stickers she passes out to a group of five men and one woman standing below a large rainbow flag just off of Market Street. The pink triangle is not just a logo Amendola uses, but, as the group will later discover, is actually one of the first symbols used by the gay community to represent themselves - not the iconic rainbow flag known to so many.

“If you don’t mind I want you to wear one of these,” she says, as the stickers make their way around the circle. “In case you get lost, the people in the neighborhood will know who to return you to,” she explains, which gets the first of many laughs from the group.

Some come from as far away as London, while others as nearby as Dolores Street in San Francisco. They’ve all gathered here for the same reason: to learn about the Castro – a neighborhood Amendola knows well.

Originally from the East Coast, Amendola has only lived in the Castro for the past five years, but she is one of its proudest residents.

As owner and guide for the Crusin’ the Castro Tour she is a walking, talking, joking encyclopedia for the sunny, flag-filled San Francisco neighborhood.

Her wealth of local knowledge combined with her own personal coming out story provides visitors and locals with insightful commentary and laughs throughout the two-hour walking journey into a neighborhood she calls “the cradle of gay culture.”

Wearing blue-tinted sunglasses, Amendola begins the tour in the Harvey Milk Plaza, named after the United States’ first openly gay elected official and former San Francisco supervisor. Milk is an icon in gay culture. A series of black and white photographs in the plaza chronicle his life, from his early hippie days to his fight for gay rights to his assassination after only 11 months in office. The tour ends at 575 Castro Street, the site of Milk’s former camera shop where a memorial plaque is embedded in the sidewalk along with his ashes.

During her tour she gives a brief history of gay culture in America. from the Gold Rush days to the mid 1900s when homosexuality was still a criminal offense in most of the United States. It was then considered a mental illness requiring shock therapy and other treatments in order to “cure” the men and women “afflicted.” To the monumental year of 1973 when the American Psychiatric Association finally announced that homosexuality was no longer considered a mental illness, thereby legalizing it.

“What has transpired in 34 years has been amazing,” Amendola says.

Equally amazing is the information Amendola provides about the Castro itself. The neighborhood, which runs from Castro Street, five blocks up and down 14th to 21st street, sits in the mouth of a volcanic crater. It was also once an Irish, Italian and Scandinavian Catholic community called the Most Holy Redeemer parish until the 1960s, when the push to buy bigger homes in the suburbs emptied the neighborhood.

The Summer of Love in 1967 ushered in a wave of hippie flower children in the Haight-Ashbury district, including Milk and his boyfriend, who moved into the Castro after a few years along with another couple and, within about two years, 20,000 gay people moved into the neighborhood and bought real estate.

Amendola seems to know everyone in the neighborhood, from the local police officer strolling by to a fellow member of Merchants of Upper Market & Castro she runs into on the way to Noe Beaver Park, a private community garden visited during the tour.
Other tour spots include the Castro Theatre and its former location (now Cliff’s Variety Store), a now empty storefront that once served as the birthplace of the AIDS memorial quilt, Twin Peaks (one of the older gay bars in San Francisco and the first to have a glass front) and Pink Triangle Park, the only place in the U.S. dedicated to LGBT individuals held in concentration camps.

One of Amendola‘s favorite spots is at the intersection of Castro and Market streets. The corner offers an unobstructed view of Twin Peaks and the many waving rainbow flags lining the Castro. The deceptively scenic spot is also popular with some of the tourists she guides. “It’s the first [picture] I took when I got here,” Michael Fischer says. Fischer is visiting from Minneapolis and originally heard about the tour from his friend Al Smith, who recently moved to San Francisco from Park City, Utah. Smith took the tour once before as a new visitor to the city and, despite his background as a history teacher, learned some new details about the Castro from the tour. Teaching about homosexuality and alternative lifestyles wasn’t allowed when Smith taught.

“[Amendola]'s got some insights that I don’t know,” Smith says.

Amendola bought the business two years ago from its longtime owner, Trevor Hailey, who decided to sell the tour after 15 years. At the time, Amendola was between jobs, but her two decades of travel industry experience, along with her political involvement in the gay community, Amendola says, made her “an awesome fit.” Hailey had a lot of offers on the tour after a story ran in the San Francisco Chronicle about it being up for sale.

“[Amendola] was actually the first potential buyer I talked with and no one else even came close to impressing me with why they wanted to buy the tour as she did,” Hailey says in an e-mail interview.

The training process, like the matching process, was fairly simple. Amendola accompanied Hailey on a few tours before she had the facts down.

“I have just a very good memory of historical things, so it’s very easy for me to pick up and remember,” Amendola says.

Most of the information Amendola talks about on the tour are similar to the topics covered by Hailey during her 15-year stint on the job, but what sets Amendola apart is that she also discusses gay culture and its sexual fluidness.

“The gay culture is very pro-sex. We love sex and we’re very proud of our sexuality,” she says. While heterosexual society may be a bit more up tight when it comes to expressing one’s sexuality, Amendola says that within gay culture there are no rules in regards to sexuality.

However, she wasn’t always so out and proud. The New Jersey native describes her former self as a very feminine girly-girl, who dated men and lived with women. She was never really sure or had the courage to be open about her sexuality. When she lived in Maui between ages 23 to 39, she went through life as a self-described bisexual homophobic lesbian. It wasn’t until she was 39 that she finally felt ready to come out. “I didn’t just come out of the closet, I mean I’m like screaming lesbian off the rooftops,” she says.

She decided that she needed to get off the island, but she didn’t want to go back to the East Coast “because there’s a million gay people in New York but there’s no community.” She wanted to not only come out, but also to make a difference by helping others to do the same.

Owning and running the tour has given Amendola the best of both worlds.
The strong sense of community among those living in the Castro is something Amendola tries to emphasize to the groups she leads through the district – where being proud of one’s sexuality is a 24/7 affair.

“It’s not a straight community where gay people live, it’s a gay community where some straight people live,” she says.