Jai Henrietta still remembers the first time she went on an Olivia Travel vacation: “I just stood there with my mouth open. Seeing 2,000 women in one space, all cuddling, holding hands, and kissing – it was a utopia for me.”
Henrietta has now traveled six times with Olivia, the world’s first travel company for lesbians. Her partner, Lyla Row, has been on 13 Olivia trips. For Row, the company takes away that “extra precaution” the couple otherwise has to take on holiday as a same-sex couple. “It’s relaxing, and that’s what a holiday should be – you shouldn’t be worrying about anything else,” she says.
The Olivia brand, which was launched in 1973 as a radical women’s record label, celebrates its 50th anniversary this year. Since the company started offering cruises, in 1990, it has hosted more than 350,000 LGBTQ+ women on cruises and resort holidays from Europe to Africa and has earned a revered status among lesbians: in 2004, the premiere of the groundbreaking lesbian TV series The L Word was held on an Olivia cruise. (An entire episode – Land Ahoy – was also set on one of its ships.) The Grammy winners kd lang, Melissa Etheridge and Mary Chapin Carpenter have performed at Olivia’s events. The tennis legend Billie Jean King has been a guest speaker seven times. Months before her death, Maya Angelou gave one of her last public speeches at an Olivia summit.
Along the way Olivia Travel has birthed long friendships and, naturally, plenty of romance. In 2015, Donna Shands was working for Olivia when she saw a guest, Cassandra Butler, walking alongside the pool. “It was almost like a cartoon character where your eyes go ‘boing!’” says Shands, who also set up Olivia’s dedicated programs for women of colour. “She had on a cute little bathing suit.” The two talked for an hour in the pool, with Butler saying: “It was a real connection.” They are now married and live in Maryland. (Shands has also officiated a wedding for a couple who met on an Olivia cruise.)
Performing with Olivia helped the comedian Gina Yashere to publicly come out. “It definitely helped to make me more open about who I am because I wasn’t that open before,” says Yashere. “I was like: ‘Well, I’m doing these Olivia trips, I might as well just be who I am.’” She recalls that raucous-sounding, first trip to an all-inclusive resort in Cancun, Mexico, in 2010. “It was like spring break for women … I was so drunk. I ended up falling in my own suitcase!”
Since that first cruise in 1990, a four-night stay in the Bahamas, Olivia has established itself as one of the leaders in the LGBTQ+ travel industry. The company offers a range of all-inclusive vacations, from cruises carrying as many as 1,400 guests to small riverboats, alongside resorts and safaris. The entire ship or resort is hired out for each trip, a strategy intended to ensure guests feel free to be themselves. “The most important thing Olivia does is create an environment where women come and feel stronger when they leave,” says Judy Dlugacz, president of Olivia Travel, who’s been there since the beginning. Last year, Olivia Travel ran more than 30 trips, including to a resort on Providenciales, in the Turks and Caicos archipelago, and from Berlin to Budapest on a riverboat cruise.
Such joyful moments very nearly didn’t happen. In the late 80s, Dlugacz was on the cusp of shutting down Olivia Records, the California-based independent label she’d co-founded with a collective of nine other radical lesbians, which boldly celebrated lesbian relationships at a time when mothers risked losing custody of their children by coming out. As Cris Williamson, a founding member who still performs with Olivia, remembers, at the time “lesbians were losing their jobs, their children, their incomes”.
She looks back on those days with pride, remembering fearless moves such as the release of a 1977 “Lesbian Concentrate” compilation, in response to an anti-gay campaign by the singer Anita Bryant. (Bryant was also an ambassador for Florida’s citrus industty.) “We were just so bold about it,” she says.
Though Olivia Records sold over a million records, by the mid-80s the collective had disbanded, leaving Dlugacz as the only remaining founder. Money was always an issue; “Olivia had survived out of pure love and gumption,” says Dlugacz. And so, after a series of 15th anniversary concerts, including a sold-out show at Carnegie Hall in New York, she planned to announce the end of Olivia Records. Only, of course, that’s not what happened.
Instead, at the first of those 15th anniversary concerts, in Seattle, Dlugacz marveled at the energy of the 2,000-strong crowd of women. “I’m going: ‘How can I stop doing this?’” she recalls. After the show, a woman came up to her and suggested doing a concert on the bay. It was this conversation that sparked Dlugacz’s idea to transform the Olivia brand into a travel company.
Dlugacz wrote to the Olivia Records mailing list. She advertised a four-night cruise to the Bahamas and needed six hundred women to do it. It sold out. When she offered a second cruise, the same thing happened. “There was so much discrimination against women, and lesbians in particular, that we wanted women to feel free to come out and be themselves,” says Dlugacz.
Finding a liner to host hundreds of lesbians was another challenge. “No one wanted to charter a ship to us,” she says. One agreed, only to pull out. In the end, Dlugacz found a Greek family cruise line. She recalls a heartwarming exchange with the captain when he – to reassure her – asked her where Sappho was from, the ancient poet having written of her love for women. “I hesitated,” says Dlugacz, “and he said, ‘The isle of Lesbos [from where the word “lesbian” is derived], and that is where I am from. So there will be no problems on this ship!’” In February 1990, the first Olivia cruise set sail.
The reception to a lesbian cruise company in the 1990s was mixed, to say the least. Initially, the word “lesbian” wasn’t even used in Olivia’s branding. “We had an understanding of how careful we needed to be to protect the women that were part of us,” says Dlugacz. For years, correspondence was delivered in plain brown wrappers. Many women traveling on Olivia’s cruises weren’t out at home.
Dlugacz remembers being on the talk show Geraldo in the early 90s, after which Olivia’s phone lines were ringing off the hook. “Half of them are calling to say: ‘I’ve never heard of this. I want to know more about Olivia! How can I go on these trips?’” she says. “Then the other half are going: ‘Suck my dick.’” In 1998, an Olivia cruise ship was met by more than 100 anti-gay protesters at a port in the Bahamas. When Dlugacz demanded an apology, the director general of the Bahamas tourism ministry came on board to say sorry to the passengers.
In the decades since, Olivia Travel has built up a loyal customer base, particularly among professional women in their 30s and older. (Prices per person range from $999 for a seven-night stay on a larger cruise to as high as $12,399 for a week-long luxury cruise on a small ship in Tahiti.) In catering to LGBTQ+ women more broadly, its guests have included transgender women, non-binary people and even heterosexual women. “Olivia, as a brand, as a company, is so strongly about the female experience,” says Dlugacz. “So, however you feel you fit into that, you belong.” The company’s trips have included countries where LGBTQ+ people are criminalized or face legal barriers – including Russia, Tanzania, and Kenya – allowing guests to go to places where they might not have gone alone.
Olivia has steered through its fair share of choppy waters. In 2009, the company settled a lawsuit out of court, filed against it by a former CEO, Amy Errett, who disputed her ownership interest. Court documents showed Errett was keen to push Dlugacz out of her role. (“We were almost gone,” Dulgacz says of that time.)
The Covid-19 pandemic halted cruises for two years, though events were moved online. It has also shifted societal attitudes. “We make an impact just by being good citizens out there,” says Dlugacz. An Olivia cruise in 1999 to Turkey saw its guests spending good money in the rug and jewelry stores of Kuşadası, winning over the local press. When the ship reached Istanbul, Dlugacz says, “the gangway opened and the paparazzi of Istanbul were there: TV cameras and the reporters, every morning newspaper. We go to the Grand Bazaar – 400 lesbians. I’m going: ‘Oh no, what is this going to be like?’ We go inside, and I’m a little worried. Everyone had read their morning newspapers and they all started going: ‘Lovely lesbian ladies, come to my shop!’”
After half a century, the Olivia brand sails on: forthcoming trips include France, the Galápagos Islands, and New Zealand. When Dlugacz co-founded Olivia, she was 20. Now she’s 71. How does she feel? “It has been my life’s work,” she says. “And I have never been bored by it.”
Dlugacz says that at its heart, Olivia Travel empowers LGBTQ+ women, for many of whom there is little visibility back home. “The women who go back out to their own communities, a lot of them live in the south or live in suburban environments that are not cities,” says Dlugacz. “There is a lot of isolation still for lesbians everywhere.”
Butler, who, at the time of her first Olivia cruise, was living in a town in Florida with little in the way of an LGBTQ+ community, says things changed after her first trip. “I accepted myself before,” she says. “But [I] always hid a little bit of it back because I was always kind of blending into a straight world. For me, honestly, it has allowed me to feel more confident in life in general.”
• This article was amended on 25 May 2023 because an earlier version said that Anita Bryant was an ambassador for the orange juice industry. To clarify: she represented Florida’s citrus industry.
