The pool water was cold. Mason (he/him) knew that going in. What he didn’t expect was the feeling on the other side, surfacing shirtless, chest scars visible for the first time, surrounded by strangers who didn’t look twice. He has one word for it. “Free,” he says. “Just free.”
Mason, a 35-year-old photographer from Cincinnati, was sailing as a staff member on VACAYA, an LGBTQ+ vacation company that offers a host of full-ship charters and vacation experiences for queer travelers and their allies. He is also transgender, and his experience at sea is part of a growing story about what affirming travel can mean and make possible for trans people right now.
Mason looks out at sea during a VACAYA charter VACAYA
It wasn’t always this way. Before finding their way to queer travel charters, many trans cruisers describe mainstream sailings as exercises in endurance. Michael (he/him), 70, a retired medical transcriptionist from Norton, Ohio, who identifies as a trans gay man, traveled for years on “straight cruises” with his husband. “We ate by ourselves,” he recalls. “We just did excursions. Mainly family-oriented type stuff.” The word he reaches for, when asked how it felt, is simple: “Isolated.”
Jamie (she/her), 42, a technology professional who identifies as a transsexual woman, had a different experience on straight cruises — and in some ways, a more disorienting one. She passed. She was read as a wife, welcomed as part of a couple, and treated warmly. “There was a lot of validation,” she says. “But the whole time it was like I was pretending.”
“All” Aboard
Stepping aboard a VACAYA ship, Jamie says it feels like “half the work’s already done.” She describes the many years she’s spent managing her presentation, watching her voice and bracing for any awkward interaction with a stranger. On a queer charter, she gets to leave most of that at the dock. “I just get to walk in with my guard down.” Jamie is still closeted at work; her professional life has no record of her gender identity history. A week at sea is the one place that changes. “I’ve got a week or two that I just don’t have to worry about pretending I don’t have a past.”
Chelle (they/them), 46, a nonbinary accountant from Fort Bragg, North Carolina, knows that the threshold of connection within the community begins long before they step onto the gangway. A veteran of nine Olivia cruises, with two more already booked, Chelle relies on the Olivia Facebook group to connect with other trans and nonbinary people who have booked the trip. “I let people know: ‘Hey, I’m Chelle, I’m nonbinary. Are there any other trans or nonbinary people going on this trip? I want them to be able to meet you.’” The Olivia Facebook group for each sailing becomes a place to locate community, signal safety, and to ensure no one boards alone.
Mason describes the contrast between life on the ship and life off it in almost jarring terms. On board, he says, the VACAYA staff greets a guest every time in the hallway with a smile, often asking if anything is needed. “I get off the ship, and I do it in real life,” he says, “and it’s like, people just stare
at me.” The warmth that feels ordinary at sea becomes, on land, a kind of culture shock in reverse.
Michael has found something similar with Brand g Vacations, the small-ship travel company he now sails with exclusively. After years of large mainstream cruises where he and his husband kept mostly to themselves, the difference was immediate. The guides learned his name, his history, and his physical needs after double hip replacements. When he returned for another sailing, they already knew him. “It just feels like a family environment,” he says. For a man who spent decades in a state where he cannot legally change his gender marker, and who came out as a trans gay man at 53, the word family is not a figure of speech.
Freeing the Body
It was on a trip with Brand g that Michael describes the first time in his life he had ever swum with other men with his shirt off. His chest bears significant scarring from multiple surgeries.
Before getting in the pool, he pulled aside one of the Brand g guides, someone who had gotten to know him over multiple trips and had watched him grow into himself as a trans man, and expressed his anxiety. He worried the other men would stare, or make him feel othered. The guide reassured him. And then he got in the water. “They just saw me as a guy. It’s just so freeing to be authentically yourself. Finally, I can be myself.”
Michael is not alone in that feeling. For Mason, the moment came on an early VACAYA cruise with his spontaneous jump into the ship’s pool, shirt off, scars visible, in front of strangers. “It really was a free and liberating feeling to feel like I am safe enough to expose who I am,” he says.
On their second Olivia trip, Chelle watched another guest with top-surgery scars walk the beach without hesitation. That was the signal. If they can do it, Chelle thought, so can I. “It was very euphoric,” Chelle says. “I felt like a completely different person.” And for Jamie, the freedom was quieter but no less profound: “I don’t need to worry about my voice, and I don’t need to worry about how I look.” Four different journeys, one unmistakable feeling of relief.
Chelle relaxes on a hammok on the beachChelle
Full Disclosure
Not everyone arrives at these experiences equally, and Jamie is the first to say so. “I was born with a lot of privilege,” she acknowledges, “and I leveraged that privilege throughout my life to put myself into a position where I have the privilege to spend the money to go on these kinds of escapes.” She is not offering financial advice, she is careful to note. But she is offering an invitation. “If you are considering trying to find a space, and you do have the opportunity or the privilege, I think it’s worth exploring.”
For those who can access it, she adds one more piece of counsel for first timers: “Understand that there will still be microaggressions, even in the safest space. Being trans is not fully understood, and there’s no blanket answer.” She leaves first-timers with one more thing to hold on to: “Know that the staff there want you there. You are a rare commodity, and you will be celebrated.”
Jamie (right) takes a diveJamie
The Best Bon Voyage
It’s clear across queer charters that the infrastructure is growing to match the feeling. VACAYA’s Transcend Lounge, a dedicated space for trans and nonbinary guests within each of its full-ship charters, is expanding every year. Olivia’s trans and nonbinary meetup group, which Chelle helped build from a handful of people into a standing community, shows no signs of slowing down. The trans and nonbinary spaces within these queer communities are getting bigger, more visible, and harder to miss.
For Chelle, the feeling never gets old. Every time a sailing ends, standing at the airport and dreading reentry into the real world, they think back on the week. “That was the greatest week of my life,” they say. “I can’t believe I did it, and I can’t wait to do it again.”
Mason, now dreaming of joining the VACAYA team full time, says he has stopped imagining what it would feel like to belong somewhere. He already knows. “I found my home,” he says. “I found my community. Some of the people that I have met are people that I know will be in my life forever.”
The water, it turns out, was the easy part.
Book That Cruise:
Olivia’s 2027 XOXO Caribbean Cruise
February 13-20, 2027
Ship: Holland America ms Eurodam
Celebrate love with 2,100 lesbians and LGBTQ+ women
www.olivia.com
VACAYA’s Caribbean Cruise 2027
February 14-21, 2027
Ship: Celebrity Beyond
Join more than 3,200 LGBTQ+ sailors for VACAYA’s 10th birthday season
www.myvacaya.com
Brand g’s 2027 Luxury Greek Isles and Turkey Cruise
September 12-23, 2027
Ship: Atlas Ocean Voyages’ World Traveller
Explore the Greek Isles with all-LGBTQ+charters
www.brandgvacations.com
VACAYA’s 2028 North Pole Expedition
August 5-17, 2028
Ship: Ponant’s Le Commandant Charcot
First-of-its-kind LGBTQ+ journey to one of the rarest coordinates on Earth
www.myvacaya.com
