TRAVEL · CARIBBEAN
Tryst launches gay cruises: a Halloween sailing in 2027, a 5,800-guest ship in 2028
The gay hotel group behind The Tryst Puerto Vallarta is taking over two whole ships in the Caribbean, with The Abbey and Fire Island venues on board. Bookings are expected to open in late November; prices aren't out yet.
Tryst Hospitality, the gay hotel and nightlife group founded by Tristan Schukraft, has announced Tryst Cruises with two full-ship gay charters in the Caribbean, in a press release dated 26 October. The first sails from Fort Lauderdale on 31 October 2027, Halloween, for six nights with 3,200 guests. The second leaves Miami on 4 February 2028 for seven nights with 5,800, which the company calls "the largest gay cruise in history".
Two ships, two routes
The Tryst Cruises website names the ships: Celebrity Beyond for the maiden voyage and Royal Caribbean's Wonder of the Seas for February 2028. The press release itself said the winter ship would be announced later. The maiden voyage, 31 October – 6 November 2027, calls at Puerto Plata and Samaná in the Dominican Republic and at Nassau in the Bahamas, closing with a party at a private Bahamas beach club. The 2028 sailing, 4–11 February, stops at Samaná, San Juan (Puerto Rico) and Philipsburg (St Maarten), according to the site.
What's on board
The pitch is to bring Tryst's land venues to sea. The release lists a takeover by The Abbey, the West Hollywood bar the group owns, Low Tea from Fire Island's Blue Whale, drag brunches, a pool club with go-go dancers, an open-air area modelled on Fire Island's Meat Rack, and a party inspired by MISTR, the PrEP telehealth company Schukraft also founded. On the decks, the release names Evita, Daddy Issues, Summertramp, Masterbeat and STAMP. The opening night is a Halloween party, which the company bills as the "sexiest party at sea". That is a claim we'll leave the passengers to judge.
Read before you plan
Fares have not been published. The website says bookings are "expected to open in late November", with a monthly payment plan from $99 per person down and "Founder Rates" not yet priced; early-access registration is open now. The first 300 guests to book get an invitation to a VIP programme called Tristan's Buoys Club, the release says.
On the "largest ever" claim: it depends on the February 2028 ship selling out, and gay charters have used ships of this size before. Atlantis Events' 2011 sailing on Allure of the Seas carried nearly 5,400 guests, NBC Miami reported at the time, as summarised by GayPV. Atlantis also chartered Oasis of the Seas in 2020, 2022 and 2024 (Wikipedia).
If you are weighing a 2027 Halloween at sea, register now, but wait for fares, cabin categories and cancellation terms before committing. Check passport and entry rules for the US departure ports and each island as the date approaches.
Sources
Facts, dates and prices in this article were checked on 28 October 2026 against the official and press sources linked in the text. Promoters' and companies' claims are attributed to them. Details can change, so check the official links before you travel or buy tickets.