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    Cruisin’ the Castro Walking Tours Honored as First San Francisco Legacy Business Tour Company

    The San Francisco Small Business Commission last month unanimously approved Cruisin’ the Castro Walking Tours as the city’s first and only Legacy Business Tour Company. Founded in 1989 by historian Trevor Hailey (1941–2007) and now owned and operated by talented travel professional Kathy Amendola, the company was recognized “for providing 30 consecutive years as a longstanding, community-servicing business and a valuable cultural asset to the city and county of San Francisco.”

    It was placed on the Legacy Business Registry on June 24. 

    The Orator of the Castro

    Hailey was born Dorothy Evelyn Fondren in Jackson, Mississippi. Later nicknamed “Skinless” by her friends and family, in part due to her openhearted spirit and hunger for adventure, she became a Navy nurse and traveled to the Philippines, was of service on a hospital ship, and then traveled to the Bay Area. It was here that Trevor Hailey was born with her embrace of the LGBTQ community. She became an activist and later earned a master’s degree in recreation and leisure before creating the walking tour

    Photo by JP LOR

    Her obituary at Legacy brings back fond memories of the charismatic tour guide: “As Trevor Hailey, she blended a unique sense of history of the Castro District with humor and a raspy, Southern voice, resulting in an entertaining and informative walking tour of this historical community.”

    Amendola, who purchased the business after Hailey’s retirement in 2005, told the San Francisco Bay Times, “Trevor became an icon as well as the orator of the Castro community for 16 years.”

    Passing the Torch

    Amendola brought years of travel industry experience to the business, nurturing its success and enabling its longevity. Her career began at Thomas Cook Travel in New York City. She subsequently worked for luxury resorts on Maui for 6 years before transferring to San Francisco’s Hotel Palomar (now Hotel Zelos) in 1999.

    As for Hailey, the move to San Francisco sparked greater LGBTQ community involvement. Amendola served as a board member for the Golden Gate Business Association (GGBA), the Merchants of Upper Market & Castro (MUMC) and the Rainbow Honor Walk project, where she remains an emeritus board member. Since purchasing Cruisin’ the Castro Walking Tours, her mission is not only to educate people on LGBTQ culture, but also to raise awareness that equality is a human right, and not a privilege. 

    Changing the World One Heart at a Time

    Amendola said, “It’s been a tremendous opportunity for me to call the Castro community my home. So much of LGBTQ history, activism and culture started in San Francisco. Over the past 14 years, my job went from being a tour guide to a civil rights activist. And following pioneers like Del Martin, Phyllis Lyon, Harvey Milk, Cleve Jones and Carol Midgen is a tremendous honor.”

    “As a diverse culture, we don’t have visibility or equal rights in America nor many parts of the world where homosexuality/diversity is still illegal, or worse, a death sentence,” she added. “My tour gives people the education and knowledge to make differences in their lives and communities. This is how we change the world, one heart at a time.”

    Her favorite story to share includes the Pink Triangle Park & Memorial and the rose quartz stones that fill the triangle. Visitors are encouraged to take the stones and to spread pride throughout the world. One tourist from Germany, Kai Klose, a member of the Green Party in the German Parliament, was so inspired that he returned to Germany and decided to come out as LGBTQ at his job. For 7 years, Klose carried his rose quartz while making speeches in the Parliament about incorporating LGBTQ laws into Germany’s government.

    Amendola, who has stayed in touch with Klose over the years, said, “In 2017, Germany legalized same-sex marriage and it was his party that was the forefront of the whole movement!”

    Image Courtesy of

    Weathering Threats and Reflecting the Evolving Castro

    Amendola notes that, over the past 30 years, the Castro neighborhood has changed as the spectrum of sexuality and gender diversity has become more visible. She said, “No longer an exclusively white, male, homosexual haven, the emergence of bi-sexuality, pansexuality and a-sexuality—to name a few—has become much more prevalent in straight looking people.”

    Community involvement remains important to her. Noting her professional achievements, the San Francisco Police Department in 2017 began hiring her to train their new cadet classes. To date, over 400 new officers have received LGBTQ cultural training to better understand and service our community.

    Photo by JP LOR

    Through the decades, it hasn’t always been easy for the woman-owned tour business. It has weathered the ebbs and flow of the economy, political tugs of war pertaining to LGBTQ rights, the deadly AIDS epidemic and more. The biggest threat according to Amendola, however, has been the rash of “free or pay as you please” tour companies—some of which have big advertising budgets and volunteer guides. She shared that many are uninsured and most are “illegally operating without San Francisco tour guide licenses.” She said, “It’s tremendously hard for any business to compete against ‘free.'”

    Nevertheless, Cruisin’ the Castro Walking Tours has thrived and continues to be a highly respected and award-winning company that offers what is arguably the most comprehensive LGBTQ tour in the world. It is a rare and exceptional San Francisco business created by two passionate women spanning 30 years. Through their colorful characters, heartfelt stories, cultural knowledge and political activism, they’ve lived history, and like ripples, continue to change history.

    Cruisin’ the Castro Walking Tours offers tours for the public on Tuesday, Wednesday, Friday and Saturday from 10 am to 12 pm. Private educational, corporate and group tours are available upon request. For more information, visit