Tryst Hospitality, the company behind The Tryst Puerto Vallarta, one of the best gay hotels in Puerto Vallarta, is heading to sea. On October 26, 2026, founder Tristan Schukraft announced Tryst Cruises: two full-ship gay charters, a 3,200-guest Halloween maiden voyage in 2027 and a 5,800-guest winter sailing in February 2028 that the company calls the largest gay cruise in history. Here is what’s planned, how the “largest ever” claim stacks up, and what it means if Puerto Vallarta is on your travel calendar.
Quick Facts: Tryst Cruises
| Maiden Voyage | Grand Voyage | |
|---|---|---|
| Dates | October 31 – November 6, 2027 (6 nights) | February 4–11, 2028 (7 nights) |
| Departs | Fort Lauderdale | Miami |
| Guests | 3,200 | 5,800 |
| Ports | Puerto Plata and Samaná (Dominican Republic), Nassau (Bahamas) | Caribbean, to be announced |
| Ship | Not yet named | To be announced |
| Booking | Early-access registration at trystcruises.com; prices not yet announced | |
Table of Contents
The Two Tryst Cruises
The Tryst Maiden Voyage: Halloween 2027
The first sailing leaves Fort Lauderdale on Halloween, October 31, 2027, with 3,200 guests on a six-night Caribbean route to Puerto Plata, Samaná and Nassau. It opens with a Halloween party and ends with a closing party at a private beach club in the Bahamas, with a surprise celebrity performance. In between, Tryst plans to bring its venues on board:
- A full takeover by The Abbey from West Hollywood, with its cocktails and dancers
- The Blue Whale’s Low Tea from Fire Island, and Fire Island’s Meat Rack reimagined in a private open-air section of the ship
- The Tryst Pool Club from The Tryst Puerto Vallarta, with its go-go dancers and DJs
- Drag brunches and shows starring the Tryst All Stars
- A Blue Ball party inspired by the MISTR boys
- Parties and DJs from Evita, Daddy Issues, Summertramp, Masterbeat and STAMP, plus live music and comedy
The Tryst Grand Voyage: February 2028
The second sailing, February 4–11, 2028 from Miami, is the headline: 5,800 guests for seven nights. The press release calls it both The Tryst Grand Voyage and The Tryst Winter Escape. The ship, the Caribbean itinerary and the onboard program will be announced later.
Is It Really the Largest Gay Cruise Ever?
If it sells out, yes. Atlantis Events set the earlier benchmark in February 2011, when Royal Caribbean’s Allure of the Seas sailed from Fort Lauderdale with nearly 5,400 gay and lesbian guests, as NBC Miami reported. Atlantis is listed to return to Allure of the Seas in March 2027 with more than 5,600 guests. At 5,800, Tryst’s February 2028 sailing would edge past both, but the ship hasn’t been named yet, so the final number depends on which ship Tryst books and how many cabins it fills.
The Puerto Vallarta Connection
For Puerto Vallarta, the story starts on Púlpito Street. Schukraft bought the former Abbey Hotel building in the Zona Romántica in early 2024 and reopened it in fall 2024 as The Tryst Puerto Vallarta, a 55-room luxury hotel designed for LGBTQ+ travelers, with a rooftop pool and bar, weekend drag brunches and DJ pool parties. In the announcement, Schukraft credits the PV hotel with changing minds about gay hotels, saying he had “reimagined what a gay hotel could be.”
That Puerto Vallarta formula is going to sea. Tryst Cruises and Tryst Hotels are both part of Tryst Hospitality, and guests will find elements of The Tryst Puerto Vallarta on board: the Tryst Pool Club, its go-go dancers and its drag entertainers. The PV hotel is named among the venues joining the ship, alongside The Abbey, Fire Island’s Pavilion and Blue Whale and Provincetown’s Crown & Anchor.
Does Tryst Cruises Stop in Puerto Vallarta?
No. Both sailings leave from South Florida and cruise the Caribbean, so Puerto Vallarta isn’t on either itinerary. To experience the Tryst style in Mexico, stay at The Tryst Puerto Vallarta itself, or book one of Puerto Vallarta’s own gay boat tours and beach parties.
Planning Around Puerto Vallarta’s Gay Calendar
Both sailings fall during busy weeks in Puerto Vallarta, so if you’re choosing between the two, check the dates:
- Halloween 2027: the maiden voyage (October 31 – November 6) overlaps Puerto Vallarta’s Halloween and Día de los Muertos week, one of the biggest party weeks of the fall. See Halloween and Day of the Dead events.
- February 2028: Puerto Vallarta Bear Week usually falls in late January or early February. BeefDip’s 2027 Bear Week runs January 24–31, 2027; the 2028 dates haven’t been announced, so check our Bear Week guide before you book the Grand Voyage.
How to Book Tryst Cruises
Early-access registration is open at trystcruises.com, and announcements are posted on Instagram at @tryst.cruises. Prices haven’t been released. The first 300 guests to book receive an invitation to Tristan’s Buoys Club, a VIP program with private gatherings and onboard perks.
Where to Stay in Puerto Vallarta
If you’d rather have the Tryst experience on land, The Tryst Puerto Vallarta is in the heart of the Zona Romántica, steps from the gay bars and Playa Los Muertos. Puerto Vallarta doesn’t have a gay all-inclusive resort, but it does have more gay and gay-friendly hotels than almost anywhere in Mexico. Compare them in our Puerto Vallarta gay hotels guide.
❓ Frequently Asked Questions
What is Tryst Cruises?
Tryst Cruises is a new line of full-ship gay charters from Tryst Hospitality, owner of The Tryst hotels and The Abbey. The first sailing is October 31 – November 6, 2027 from Fort Lauderdale; the second is February 4–11, 2028 from Miami.
Is it the largest gay cruise ever?
At 5,800 guests, the February 2028 sailing would top Atlantis Events’ record of nearly 5,400 guests in 2011 and its 5,600-plus sailing listed for March 2027, if it sells out.
Does Tryst Cruises stop in Puerto Vallarta?
No. Both sailings depart South Florida and cruise the Caribbean.
How much does Tryst Cruises cost?
Prices haven’t been announced. Early-access registration is open at trystcruises.com.
Is The Tryst Puerto Vallarta a gay hotel?
Yes. It is a luxury hotel designed for LGBTQ+ travelers in Puerto Vallarta’s Zona Romántica, with a rooftop pool and bar, drag brunches and pool parties.
Is there a gay all-inclusive resort in Puerto Vallarta?
No. Puerto Vallarta has many gay and gay-friendly hotels, but no gay all-inclusive resort. See our gay hotels guide for the options.
Sources: Tryst Hospitality press release (GlobeNewswire, October 26, 2026); NBC Miami, “World’s Largest Gay Cruise Leaves South Florida” (February 2011); GayOut, gay cruises 2027;
Author: Tim Wilson
Wilson is the founder of GAYPV.com and www.gaybartour.com and has been the leading LGBTQ+ travel and lifestyle authority in Puerto Vallarta since 2005. With over two decades of local expertise, Wilson specializes in being a community advocate and leader for Puerto Vallarta , and local cultural insights that only a long-term resident can provide. He has dedicated 20+ years to advocating for safe, inclusive travel in Banderas Bay, establishing GAYPV as the region's most trusted resident insider.. His work has been cited by major travel publications, and he is widely recognized as a trusted insider voice on Puerto Vallarta’s vibrant LGBTQ+ scene.
