OMG! Jenifer Lewis surprises gay cruise goers with a Billy Porter duet

You never know what, or whom, you'll find on a gay cruise!

Mark Mark
Feb 26, 2026 - 19:00
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Jenifer Lewis and Billy Porter sing into microphones performing on stage on a VACAYA gay cruise.

You never know what you’ll find on a gay cruise: new friends scouted from the deck, romance on the sea, or a gag-worthy surprise celebrity appearance in the middle of a Jenifer Lewis concert!

That’s exactly what happened to a lucky group of 2,500 gays aboard VACAYA LGBTQ+ Vacation‘s most recent Caribbean trek, which set sail from February 14 to 21.

As the 69-year-old showbiz legend delighted guests to a performance — one of her first shows back since a harrowing near-death experience in 2022 — she stopped the set to welcome a very special guest: the one and only Billy Porter.

Watch.

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Courtesy of VACAYA LGBTQ+ Vacations

As the Pose icon sashayed up to the stage, Lewis explained that her 39th birthday party and Bette Midler, whom she started out singing back up for, played a crucial part in his rise to fame.

“[She] was there and she heard this young motherf*cker sing and that’s where he got his break,” she explained, before Porter corrected her: “One of [the breaks.]” LOL.

The close pals joked about Porter’s recent viral moment at the 2026 MusiCares Person of the Year Gala, where he passionately went off on a particularly homophobic female rapper.

“If you weren’t a star before this, you’re a star now,” Lewis quipped, before the two delivered a gorgeous rendition of gospel hymn, “His Eye Is on the Sparrow.”

Puerto Rico and the Virgin Islands might have been on the itinerary, but VACAYA vacationers were not expecting a night with the stars. We’re shook — and we weren’t even there!

So, what can I expect on a gay cruise?

While it might be too late to catch Jenifer Lewis — the FOMO is real! — you can already snag tickets for VACAYA’s 2027 Caribbean cruise, which departs from Fort Lauderdale, and will swing by Haiti, the Dominican Republic, and Saint Martin.

The LGBTQ+ travel community, which specializes in big-ship and small-ship cruises and resort stays and tours, is one of several queer and ally-focused providers leading the charge in keeping “cruise culture” gay.

Between top-notch entertainment, world-class dining, exciting ports of call, and shenanigans on the sea, moments like these remind us just how exciting these travel opportunities have evolved to be. Of course, there are the adults-only activities, but that’s far from the only option.

As @readytostare put it, these LGBTQ+-centered experiences are helping “undo this idea that our community needs separate spaces and working to build a space where we can all show up and be ourselves authentically.”

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