A big name in LGBTQ+ hotels and nightlife is heading to sea. Tryst Hospitality on Monday launched Tryst Cruises, a new brand that will run full-ship gay charters. The first sails from Fort Lauderdale on Halloween 2027, and the second, in February 2028, is billed as the largest gay cruise in history.
Two sailings, two sizes
Tryst Cruises has announced two charters so far:
| Sailing | Dates | Departs | Guests |
|---|---|---|---|
| The Tryst Maiden Voyage | Oct. 31 to Nov. 6, 2027 | Fort Lauderdale | 3,200 |
| The Tryst Grand Voyage | Feb. 4 to 11, 2028 | Miami | 5,800 |
A full-ship charter means one group books the entire ship. The charter company then runs its own entertainment, parties and events on board.
The Halloween maiden voyage
The first trip is a six-night cruise called All Hands on Deck. It leaves Fort Lauderdale on October 31, 2027. The ship will call on Puerto Plata and Samaná in the Dominican Republic, and Nassau in the Bahamas.
The cruise opens with a Halloween party. Tryst says the trip will bring its best-known venues and events on board. Highlights it lists include:
- Parties and DJs from across the Tryst brand, including Evita, Daddy Issues, Summertramp, Masterbeat and STAMP.
- A full takeover by The Abbey, the West Hollywood bar, with its cocktails and dancers.
- Low Tea from The Blue Whale on Fire Island.
- Drag brunches and shows with the Tryst All Stars.
- Live music and comedy from LGBTQ+ performers.
- The Tryst Pool Club, with DJs and dancers.
- A closing party at a private beach club in the Bahamas, with a surprise celebrity performance.
Tryst did not name the ship or the cruise line it is chartering for the Halloween trip.
A record-size winter sailing
The second charter, The Tryst Grand Voyage, runs for seven nights from Miami. It will carry 5,800 guests. Tryst calls it the largest gay cruise in history.
The ship, the Caribbean route and the onboard lineup for this sailing have not been announced. Tryst says those details will come later.
A VIP club for early bookers
The first 300 guests to book a Tryst Cruise will be invited to a VIP group called Tristan's Buoys Club. Tryst says it is inspired by the Captain's Table tradition. Members get private gatherings, special recognition and other perks during the voyage.
Who is behind Tryst
Tryst Hospitality was founded by Tristan Schukraft. Its Tryst Hotels brand calls itself the first luxury gay hotel brand. It has hotels in Fire Island, Rio de Janeiro, Puerto Vallarta, Provincetown, Wilton Manors, Chicago and San Juan.
The company also runs well-known bars and clubs. They include 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.
"Many people had written off gay hotels as campy or not for them until they experienced The Tryst Puerto Vallarta," Schukraft said. He said Tryst Cruises brings "the best of our destinations at sea."
What it means for cruisers
Gay charters have been part of cruising for years. Tryst says it wants to do them differently, by bringing the feel of its own venues on board rather than a standard formula.
The 5,800-guest February sailing would be a large charter by any measure. The ship for that trip has not been revealed yet.
Prices have not been released. Tryst says early access sign-up is open at trystcruises.com. Fort Lauderdale's cruise port is Port Everglades, which you can explore on our Port Everglades page.
Source: Tryst Hospitality press release via GlobeNewswire, October 26, 2026.