By Jenny Block–
I still remember my very first cruise with Olivia Travel, the travel company for lesbians and LGBTQ+ women, with such clarity. It was 2010. From the moment I got on board, I knew I had stumbled into a whole new world that I was going to love. Everyone was so welcoming and friendly. All week long I felt held. Like, here was this space where I could be myself and everyone around me could be too. It was like grown-up summer camp and I never wanted to go home.
That was fifteen years ago now, and I’ve been on more than a dozen Olivia trips since then. Every time I go, I come back renewed, reminded that the world can be gentle and kind if we choose those paths. This is a big year for Olivia Travel, which takes lesbians and LGBTQ+ women on cruises, resorts, riverboats, and adventures of all varieties all over the world.
It’s the 35th Anniversary of a concept that began when a group of women took a leap of faith and signed up for the very first cruise, a 4-night trip to the Bahamas.
“We sent a letter to our mailing list and, within a few weeks, 600 women signed up for the cruise,” said Judy Dlugacz, Founder and President of Olivia. “So, we did it again the following week and 600 more women signed up! It was the thrill of creating that first adventure. We had a blast!”
Olivia Records was already a revolutionary success, recording female artists at a time when they were grossly underrepresented in the music industry. An idea sprang forth: Why not create concerts at sea to bring the artists and fans together in a world all of their own creation? Dlugacz began by looking for the perfect ship to charter.
Once she did, Dlugacz went on an inspection cruise. The Captain asked Dlugacz to come to his office after a meeting about the upcoming trip. “The cruise company was Dolphin, which was a small Greek line,” Dlugacz said.
“The Captain asked me in a very strong Greek accent, ‘Who was the first lesbian?’ and I answered, ‘Sappho?’ He said, ‘Correct! And Sappho was from the Isle of Lesbos and that is where I am from … so there will be no problems on this ship!’”
And he was right. “I remember the very first cruise in 1990, and how happy and empowered women felt just being able to dance together on the deck for Sail-Away,” Senior Vice President of Travel Jill Cruise said.
“Later I realized that the effect was not just on our women, but on the ship’s crew; it changed so many for the good when they saw how friendly, kind, and respectful we were to them.”
That first cruise was groundbreaking and inspiring, for the women traveling and for the crew of the ship. It’s important to remember, 1990 was a very different time.
“It was a time that holding hands as lovers in public was risky; a time many, many of our guests were not out to their kids,” Olivia co-founder Rachel Wahba said. “We were not visible—and here we were visible in front of the crew, the world, and each other—it could have gone differently, but instead, within a day or so, a love affair I did not expect had formed between the gracious women and the crew.”
Dlugacz says she is equal parts thrilled and amazed at how Olivia opens the hearts and minds of so many people wherever they go and that her incredible team never takes anything for granted. That’s because Olivia Travel is about so much more than going on a vacation, although it certainly is about that too. Olivia is about modeling life as it could, and should, be.
For those unfamiliar with Olivia, all I can tell you is that it’s like a magical concoction brewed by and for the lesbians and LBGTQ+ women who are a part of the Olivia community, with a history so rich it’s downright revolutionary.
“We often say, ‘You don’t know until you go’ because there is a loving appreciation and such comradery as you step onto a ship or resort or travel the world. It’s unlike any other,” Dlugacz explains. “We create the space where we are the majority and the power of that is pretty extraordinary … even for the most jaded!”
Cruise adds, “I wish they knew the real feeling of being themselves while on vacation and the incredible community we have. One of the best parts of the trips, aside from the opportunity to travel to new places, has to be the life-long friendships people have made with each other all over the world. I love seeing our guests make new friends. I’ve watched these groups experience so much together and provide so much support in times of need.”
Some of the most pivotal moments in Olivia Travel history include a Boston to Montreal Cruise in 2004, when same sex marriage became legal in Boston, MA, and Olivia hosted a group wedding at the Four Seasons hotel in Boston and a Mexican Riviera Cruise in 2008 when same sex marriage became temporarily legal in California for a “summer of love” and Olivia conducted individual weddings for over 100 couples at the home port of San Diego.
Of course, the pandemic in 2020 was an incredibly pivotal moment for Olivia too, as it was for so many businesses and individuals. “Olivia is a survivor,” Executive Vice President and Cruise Director Tisha Floratos-Silano said. “With every trip that we had to postpone, our guests stuck with us. We navigated this storm because of our amazing office team, the Olivia guests, our travel partners, and Judy’s daily conviction to ensure Olivia survived. And we did! And we are stronger because of it!”
Naturally, celebrating the 50-year Anniversary of Olivia Records in 2023 was a big moment for Olivia as well, as is the 35th Anniversary of Olivia Travel this year. They are celebrating this milestone with their sold-out Coral Jubilee—Olivia and the world’s largest LGBTQ+ women’s cruise ever—with 2,600 Olivians sailing to the Caribbean next month. They’ll also celebrate on dry land on their Anniversary resort trip in Punta Cana this October.
Looking back, the thing that surprises Cruise the most, she says, is “the loyalty and the number of repeat travelers we have had over the years. We thought that anyone who traveled on more than 10 trips with us would be the highest VIP possible. Now we have so many who have traveled 20, 30, 40, 50, 60 plus times with us!”
Over the past thirty-five years, Dlugacz says, “So many have told me how Olivia has changed their lives. The friendships that have been started, the true loves that have been sparked. But the most poignant story I remember was from a woman who had been sexually assaulted two years prior. She told me that her experience with Olivia gave her a renewed sense of self and that she felt alive again.”
And though this 35th Anniversary is a major milestone, it’s only the beginning. “Those first 35 years went by in a flash,” Dlugacz said. “It is my hope that Olivia will be creating new and extraordinary experiences for generations to come.”
Olivia has certainly changed me. It’s emboldened me to stand in my power. It’s reminded me that I am never alone even when the world might try to make me think I am. And it’s shown me that lesbians and LGBTQ+ women are bolder and stronger and smarter than ever. We are beautiful together, as the Olivia Theme Song says, a song that still makes me cry happy tears every time I hear it. “We live our truth and we love our lives.”
And that, truly, is something beautiful.
Jenny Block is a Lambda Literary award-winning author, writer, and speaker. She is a frequent contributor to a number of high-profile publications from “The New York Times” to the Huffington Post, and is the author of “Be That Unicorn. Find Your Magic. Live Your Truth. Share Your Shine”; “The Ultimate Guide to Solo Sex”; “O Wow: Discovering Your Ultimate Orgasm”; and “Open: Love, Sex, and Life in an Open Marriage” (winner of a 2008 Lambda Literary Award). Her new book, “Badass Manifesting,” will be released on May 13. Find her online (https://bethatunicorn.com/) and on IG @thejennyblock
Olivia Travel 35th Anniversary
Published on February 27, 2025
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