Tryst Cruises Sets Sail with Full-Ship Gay Takeovers Including The Largest Gay Cruise in History

The best of West Hollywood, Provincetown, Fire Island and Puerto Vallarta. Together at sea. Halloween 2027: 3,200 sailors. Six Nights. All Hands on Deck. February 2028: 5,800 Sailors. Seven nights. One hot winter escape on the Largest Gay Cruise Ever!

San Juan, PR, Oct. 26, 2026 (GLOBE NEWSWIRE) -- Tryst Hospitality is taking its signature nightlife and hospitality to the high seas with the launch of Tryst Cruises, featuring two full-ship gay charters. The celebration begins on Halloween, October 31, 2027, when 3,200 sailors depart Fort Lauderdale for a six-night maiden voyage. From February 4–11, 2028, Tryst Cruises goes even bigger with The Tryst Winter Escape bringing 5,800 sailors together aboard one ship for the largest gay cruise in history from the largest gay hospitality company in the world.

Two sailings. Two Excuses to Pack Very Little.

“Many people had written off gay hotels as campy or not for them until they experienced The Tryst Puerto Vallarta,” says Tristan Schukraft, founder and CEO of Tryst Hospitality. “I reimagined what a gay hotel could be. With Tryst Cruises, I’m bringing together the best of our destinations at sea. Starting with 3,200 sailors on Halloween 2027, then we go bigger with 5,800 in February 2028. There’s a lot to look forward to.”

For years, large-scale gay cruises have followed the same formula. Tryst Cruises is built differently. Each sailing brings together the talent, parties and production of iconic venues from across the Tryst Multiverse, including The Abbey in West Hollywood, Fire Island’s Pavilion and The Blue Whale, The Crown & Anchor in Provincetown, and The Tryst Puerto Vallarta. From Low Tea to late-night dance floors, guests can experience the personalities and traditions that make each destination distinct, together on one ship.

The Tryst Maiden Voyage 
All Hands on Deck
October 31–November 6, 2027 | Departing Fort Lauderdale
3,200 sailors. Six nights. One ship.

Setting sail on Halloween 2027, the first Tryst Cruise is a full-scale entertainment takeover, bringing Tryst’s most iconic events and venues onboard. The full-ship, six-night sailing departs from Fort Lauderdale and stops in Puerto Plata, Dominican Republic, Samaná and Nassau.  The cruise kicks off with an inaugural Halloween party that will be sexiest party at sea.

Highlights of the first cruise include:

• World-class nightlife featuring the best parties, entertainers and DJs from across the Tryst Hospitality empire, including Evita, Daddy Issues, Summertramp, Masterbeat and STAMP
• A full Abbey takeover on the ship featuring its famous cocktails and dancers
• The Blue Whale’s Low Tea
• Drag brunches and shows starring the Tryst All Stars from around the world
• Live music, comedy and performances from the best entertainers in the LGBTQ+ community
• The Tryst Pool Club with its signature go-go dancers, DJs and more
• Fire Island’s famous Meat Rack reimagined in a private open-air section of the ship
• A show-stopping Blue Ball party at sea inspired by the MISTR boys
• A closing party at a private beach club in the Bahamas with a surprise celebrity performance worthy of The Tryst name

The Tryst Grand Voyage
The World's Largest Gay Cruise 
from The World’s Largest Gay Hospitality Company
February 4–11, 2028 | Departing Miami
5,800 sailors. Seven nights. One Very Hot Winter.

Size matters. So does what you do with it. For its second sailing, Tryst Cruises celebrates big deck energy and welcomes 5,800 sailors aboard the largest gay cruise in history. The Tryst Grand Voyage brings the Tryst Multiverse together for seven nights of nightlife, entertainment and connection on an even bigger scale.

The ship, Caribbean itinerary and onboard programming will be announced separately. Consider this your advance warning to clear your calendar.

Tristan's Buoys Club: You Came First

The first 300 guests to book a Tryst Cruise will receive an exclusive invitation to Tristan's Buoys Club, a VIP experience inspired by the tradition of the Captain's Table, with a Tryst twist. Members will enjoy private gatherings, elevated onboard experiences, special recognition and exclusive privileges throughout their voyage. With membership limited to just 300 sailors, Tristan's Buoys Club brings a new level of exclusivity to cruising. After all, there's something special about coming first.

Ready to Cruise?

Tryst Cruises is about more than where you’re going. It’s about who you’re with. Built for connection, celebration, and unforgettable nights, each sailing brings together the Tryst community in a way that can only happen at sea. From a Halloween maiden voyage to a February Winter escape with 5,800 sailors, Tryst Cruises gives guests two ways to experience their favorite destinations and discover new ones, all on the world's best ships.

Early access registration is now open at trystcruises.com. Follow @tryst.cruises for announcements, entertainment reveals and booking updates.

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About Tryst Hospitality

Tryst Hospitality, founded by Tristan Schukraft, is redefining LGBTQ+ travel and nightlife. Tryst Hotels is the first luxury gay hotel brand, with properties in premier destinations including Fire Island, Rio de Janeiro, Puerto Vallarta, Provincetown, Wilton Manors, Chicago and San Juan. The company also operates iconic venues such as The Abbey in West Hollywood, The Crown & Anchor in Provincetown, Circo Nightclub in San Juan, and The Blue Whale and Pavilion in Fire Island Pines. Beyond hospitality, Schukraft founded MISTR, a leading telehealth platform providing free online access to PrEP and long-term HIV care. Learn more at trysthospitality.com. 

Attachments

• Tryst Hospitality is taking its signature nightlife and hospitality to the high seas with the launch of Tryst Cruises.
• The Tryst Maiden Voyage | All Hands on Deck

Brian Rosman
Tryst Hospitality
323.443.7880
pr@trysthospitality.com