Tryst Hospitality, Tristan Schukraft’s company of gay hotels and nightlife venues, announced Oct. 26 that it’s starting a cruise line built on full-ship gay charters. The first Tryst Cruises sailing leaves Fort Lauderdale, Florida, on Halloween 2027, according to the company’s press release on GlobeNewswire.
That maiden voyage runs six nights, Oct. 31 to Nov. 6, 2027, with about 3,200 guests. It stops in Puerto Plata and Samaná in the Dominican Republic and in Nassau, Bahamas. The release didn’t name a ship. The Tryst Cruises website lists it as Celebrity Beyond.
A bigger sailing follows Feb. 4 to 11, 2028, out of Miami with about 5,800 guests. Tryst calls it “The World’s Largest Gay Cruise.” The website puts that one on Royal Caribbean’s Wonder of the Seas, with stops in Samaná, San Juan and Philipsburg, St. Maarten. The release said the ship, route and programming would be announced separately.
“Starting with 3,200 sailors on Halloween 2027, then we go bigger with 5,800 in February 2028,” Schukraft said in the release. “There’s a lot to look forward to.”
From The Abbey and the Crown & Anchor to Celebrity Beyond
Schukraft is best known for MISTR, a telehealth service that mails HIV prevention medication at no cost, and for The Abbey in West Hollywood, whose sale to him was announced in 2023, the Provincetown Independent reported. He started buying gay hotels in 2022 with one in San Juan, Puerto Rico. His company took over Provincetown’s Crown & Anchor last winter and is planning a Tryst hotel in Chicago’s Northalsted.
He pitched the cruises as the next step after the hotels. “Many people had written off gay hotels as campy or not for them until they experienced The Tryst Puerto Vallarta,” Schukraft said in the release. “I reimagined what a gay hotel could be. With Tryst Cruises, I’m bringing together the best of our destinations at sea.”
He made a similar case when he bought the Crown & Anchor. “Preserving queer spaces and having a space to call our own is more important now than ever,” he told the Independent last December. “When you go to a gay space where you feel safe, you’re reminded you’re not alone.”
Abbey Takeover and Blue Whale Low Tea on the Halloween 2027 Sailing
According to Tryst’s announced plans, the maiden voyage opens with a Halloween party. The Abbey is staging a full takeover on board with its cocktails and dancers, and Fire Island’s The Blue Whale brings its Low Tea. There are drag shows too. The trip ends with a party at a private beach club in the Bahamas.
The first 300 people to book get an invitation to what Tryst calls “Tristan’s Buoys Club,” a VIP program with private gatherings and onboard perks.
Every sailing is adults only, the website says. Solo travelers can sign up for a “Sailor Match” program to share a cabin.
Tryst Cruises Pricing and the Record Claim
Prices aren’t out. The website says bookings should open in late November, with a monthly payment plan starting at $99 per person down. That is a down payment, not the total fare. Fares cover the cabin, main dining, entertainment and Tryst’s events. Specialty restaurants, shore excursions, drink packages and Wi-Fi cost extra. Early access sign-up is open now.
The 5,800 figure is Tryst’s projection, and the record description remains the company’s claim. For comparison, Atlantis advertised 5,500 guests for its February 2026 Symphony of the Seas charter. Its 2027 Allure of the Seas promotion promises more than 5,700. Announced capacity is not a final passenger count.
