Tristan Schukraft, CEO of Tryst Hotels / Courtesy photo

Getting to Know Tristan Schukraft, CEO of Tryst Hotels — And Everything Gay

Rooftop pool parties, brunchtime drama, and guaranteed fabulousness are hallmarks of the Tryst Hotel in San Juan, Puerto Rico. CEO and founder of Tryst Hotels Tristan Schukraft announced that a multimillion-dollar renovation project to improve the property will be completed by next year, including the addition of a beach club, rooftop bar, and beachfront restaurant.
Following the flagship Tryst Puerto Vallarta that opened this summer, the Tryst San Juan features 33 rooms with expanded balconies and terrace suites for guests to appreciate the horizon on Condado Beach. Now accepting reservations, the Tryst is a dream come true for its founder.
Schukraft already crossed off several goals from his business bucket list — from owning world-famous gay bars, The Abbey and The Chapel in West Hollywood, to founding the PrEP delivery and telehealth service MISTR, which serves over 300,000 patients.
“When I was younger, I saw the movie, ‘The Birdcage,’ and since then wanted to own a hotel because of it,” Schukraft said in an interview with Georgia Voice. “Years later, someone pointed out to me that it was a nightclub, and now I own those too. I used to live in a hotel, which is a lot more fun when you don’t own the hotel.”
Schukraft is a leader for the next generation of LGBTQ business owners as the “CEO of everything gay.” Expanding his résumé from technology and telehealth entrepreneurship to nightlife and hospitality endeavors in recent years, Schukraft said he hopes to preserve queer spaces and offer catered experiences for gay tourists.
Situated in the most coveted locations within iconic LGBTQ travel destinations, Tryst Hotels are designed to be the epicenter of local gay culture, offering an immersive cultural experience and luxury. Each property is committed to eco-conscious practices, supporting the local LGBTQ community, and working with minority-owned businesses, ensuring that every stay contributes to the community.
“There is a generation of LGBTQ entrepreneurs looking to retire right now and the LGBTQ-owned businesses that defined our neighborhoods are turning over,” Schukraft said. “If another generation of LGBTQ entrepreneurs doesn’t buy them, our queer villages will disappear. Making sure these businesses stay operating and LGBTQ owned protects our communities.”
Curated travel destinations and lodging for the LGBTQ community can be seen in places like the Tryst and Trixie Motel — a boutique hotel founded by singer and drag queen, Trixie Mattel. However, the need for variety in accessibility and destination cannot be overstated.
While walking around San Juan, Schukraft noticed a less-than-stunning parking lot he thought would be a great space for a gay beach club. Next to it, a hotel sat waiting for its destiny to be realized as a premier destination for gay travelers.
“I looked up, and it was called the Tryst. I always wanted to own a hotel, and here was one for sale with my name on it!” Schukraft said. “Tryst Hotels lets you be your best self, even on your worst behavior. That kind of explains me. I wanted something playful, even though it’s a luxury hotel. We want you to embrace the extraordinary, one Tryst at a time.”
As an aviation enthusiast and visitor to over 100 countries, Schukraft saw a need for truly inclusive hotels for queer travelers in his excursions.
“Not all hotels are welcoming, and even the ones that are might not fully embrace that scene and crowd,” Schukraft said. “Even in resorts claiming to be inclusive, my boyfriends and I will still get side-eye from guests from sharing one room, or sometimes it’s our swimsuits at the pool.”
Along with in-house entertainment in the form of world-class DJs and Drag Brunches, patrons of the Tryst San Juan can visit Schukraft’s renovated nightclub Circo when it re-opens in the fall.
The Tryst Puerto Vallarta will open this summer in the heart of the Zona Romántica and begin taking reservations in the next few weeks. The Tryst San Juan is open now, but will begin extensive renovations later this year. Fire Island will become the brand’s third location in 2025.
“The Tryst is a gay hotel, but everyone is welcome. The only things that are straight are the martinis,” Schukraft said.
Visit or follow @thetryst_sanjuan on Instagram to learn more.