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My first queer cruise threw all expectations overboard

My first queer cruise threw all expectations overboard

My first queer cruise threw all expectations overboard
VACAYA/Gabriel Goldberg (@HollywoodBruisers)

A VACAYA Caribbean voyage offered a surprising diversity of passengers and activities, including unforgettable acts from Vanessa Williams, Daya, Alan Cumming, and Ari Shapiro.

Toward the conclusion of Vanessa Williams’s performance during the VACAYA cruise of the Caribbean in February, the “Save the Best for Last” singer searched for a musical number that she knew would be a hit for the mostly LGBTQ+ audience. From the crowd, someone yelled out, “Kiss of the Spider Woman.” Williams’s music director didn’t know the music, but Williams, who had made her Broadway debut in that musical, was inspired. “I said, ‘I’ll do it a cappella,’” Williams recalls.

The crowd hushed, the boat swayed, Williams’s voice soared, and there was an “eerie connection by the end. It was really, really unusual and unexpected and so fulfilling.”

“Those are the kind of audiences that you get on VACAYA, for sure, which — I’ve never had that experience happen before,” she marvels.

VACAYA/Gabriel Goldberg (@HollywoodBruisers)

Indeed, there were many unique experiences to be had on that VACAYA cruise, a seven-night voyage that embarked in Fort Lauderdale, Fla., and had stops in San Juan, Puerto Rico, and St. Croix in the U.S. Virgin Islands. While the destinations — and cruise-organized excursions like snorkeling — were dazzling, it was the ship itself that was special: Nearly 3,000 passengers, all of them LGBTQ+ and ally, filled the Celebrity Apex ship with pride and joy.

It was the first time this gay writer had embarked on any cruise — let alone a queer one. Until that point, my impressions of a gay cruise were influenced by what I saw on social media from some of VACAYA’s competitors, which looked akin to a high-seas circuit party.

But as soon as I boarded the ship in Fort Lauderdale, I threw those expectations overboard. This was no circuit party; it felt more like summer camp. Warm smiles and hellos from fellow guests and crew members were typical, a welcome change for this big-city resident. Although the demographic did skew toward older and male, there was notable diversity in age, body type — the bears abounded — as well as gender.

In fact, an entire “Transcend Lounge” was devoted to happenings and resources for trans and nonbinary folks. Moreover, the activities catered to a rainbow of interests, from Dungeons & Dragons tournaments to art auctions to musical sing-a-longs. And I was blown away by the cuisine aboard the billion-dollar vessel, which offered high-end dining options like its Fine Cut Steakhouse, Raw on 5, and the Eden Restaurant.

VACAYA/Gabriel Goldberg (@HollywoodBruisers)

Daya, a 25-year-old singer whose hits like “Sit Still, Look Pretty” and “Hide Away” became anthems of the cruise, enjoyed her time as a young queer female passenger — in addition to being a Grammy-winning performer who got crowds dancing on their feet. “It’s very similar to Prides that I played,” she affirms. “I feel like every generation [is represented]. It’s very diverse and very fun.”

VACAYA bills itself as “the first large-scale adults-only vacation company on earth built for the entire LGBTQIAPK community and their straight ally friends.” And indeed, the company’s founders, John Finen, Randle Roper, and Patrick Gunn, sought to create an “in-between” space that bridged the gay cruise with a mainstream vacation. As its mission statement attests on the company website, “while everyone loves a good time, there’s more to a memorable vacation than just parties.”

Performances from Williams and Daya were a memorable centerpiece of my experience. Throughout my adventure, I was also entertained by the drag performer La Voix, the comedian Alec Mapa, and Alan Cumming and Ari Shapiro, who adapted their popular Och & Oy touring cabaret act for the cruise.

VACAYA marked the first time the duo had performed their show for a queer audience since 2019, “and it does land a little differently,” Shapiro attests. Throughout their set, the NPR host and the Traitors star threw out phrases like “piss queens” and “versatile verbal pig,” aware that Vacayans (as the cruisers identify themselves), will laugh from a place of knowing versus shock.

VACAYA/Gabriel Goldberg (@HollywoodBruisers)

When Cumming tells Shapiro to save a masturbation tale for the red-light district, a reference to the sex-positive space open nightly on the ship’s pickleball court, they’re laughing from lived experience. The VACAYA audience is “really uproarious and fun,” Cumming says, noting that the “pitching” boat motion adds another topsy-turvy stage element.

Importantly, Cumming and Shapiro did not cloister themselves in their rooms outside of performances. The entertainers enjoyed the nightly theme parties that were another centerpiece of the cruise, with themes ranging from prom to cowboys to pirates. (In an unforgettable surprise, Carnie and Wendy Wilson performed “Hold On,” a la Bridesmaids, for the prom-night crowd.)

Cumming cites dancing as one of his cruise highlights. Shapiro loves the variety. “It’s a choose-your-own-adventure,” Shapiro says. “You can be as sedentary or as wild as you want to be. You can be as indulgent or monastic. I did yoga in my room, and just watching the waves go by and the bird floating outside the window was glorious.”

During window-watching in a public area, a fan approached Shapiro to offer shots of turmeric and ginger. “I looked at him and I thought, This is not somebody who’s going to dose me with [GHB]…. So I took the turmeric shot, and we had a nice little conversation.”

Learn more about VACAYA events, including upcoming cruises through Europe and Alaska, at

This article is part of the Out May/June issue, which hits newsstands on May 28. Support queer media and subscribe— or download the issue through Apple News, Zinio, Nook, or PressReader starting May 14.

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Daniel Reynolds

Daniel Reynolds is the editor-in-chief of Out and an award-winning journalist who focuses on the intersection between entertainment and politics. This Jersey boy has now lived in Los Angeles for more than a decade.

Daniel Reynolds is the editor-in-chief of Out and an award-winning journalist who focuses on the intersection between entertainment and politics. This Jersey boy has now lived in Los Angeles for more than a decade.