Tryst Global Expansion: From Chicago’s Northalsted to Puerto Vallarta’s Zona Romántica

 

Tryst Hospitality has announced plans for The Tryst Chicago, a new 21 room boutique luxury hotel proposed for the heart of Chicago’s historic Northalsted neighborhood—one of the most established LGBTQ+ districts in the United States.

Planned for the former DS Tequila site on North Halsted Street, the new hotel is the latest addition to the Tryst Hotel collection.  According to founder Tristan Schukraft, the goal is to create a destination that keeps visitors in the neighborhood—enhancing, rather than extracting from, one of the most iconic LGBTQ+ districts in the world.

👉 For deeper insight into the vision behind Tryst Hotels, read our exclusive interview with Tristan Schukraft, the “CEO of Everything Gay here

The Tryst Puerto Vallarta Reality Format

The proposal for The Tryst Chicago is already in place at The Tryst Puerto Vallarta in the heart of the Zona Romántica.  Guests don’t just check in—they step directly into one of the most walkable and immersive LGBTQ+ environments in the world.

The success of the Puerto Vallarta flagship lies in the “Tryst Lifestyle,” which focuses on three core pillars now being exported to every new location:

• Social Connectivity: Creating spaces like the rooftop pool where travelers and locals actually interact.

• Intentional Design: Partnering with firms like NEWLOOK Design to ensure every square foot feels intimate and “design-forward.”

• Unapologetic Authenticity: Creating an environment where, as the brand motto suggests, you can experience your best self, even on your worst behavior.

Think rooftop pool activations, a restaurant and nightlife component, and a design-forward space built to keep people engaged—not just passing through. It’s Tryst’s signature mix of glamour, community, and just the right amount of trouble, already fully realized.

Puerto Vallarta’s Hottest Weekly Tradition: Sunday Drag Brunch & Rooftop Pool Party

One of the heartbeats of the Romantic Zone on Sunday is  The Tryst Puerto Vallarta. What began as a local gathering has rapidly emerged as one of the most popular recurring weekly events in the destination—drawing a vibrant mix of hotel guests, expats, and visitors from across the city.

The experience kicks off with the Sunday Drag Brunch, a high-energy celebration of talent, humor, and world-class hospitality. But the magic doesn’t stop when the plates are cleared; the party seamlessly transitions into a high-energy rooftop poolside continuation that keeps the energy soaring well into the afternoon.

A Shift in the Puerto Vallarta Social Scene

This kind of seamless daytime-to-evening programming reflects a larger shift in Puerto Vallarta’s tourism landscape. Today’s LGBTQ+ luxury traveler is looking for experiences that aren’t limited to late-night dance floors. At The Tryst, the social scene extends across the full day, offering a sophisticated yet wild atmosphere under the Mexican sun.

The Tryst Programming: From High-Energy to Intimate

Together, these concepts show how The Tryst is masterfully segmenting its entertainment to offer something for every mood:

• The Social Hub: High-energy, communal, and loud (The Sunday Drag Brunch + Pool Experience).

• The Sophisticated Night: Intimate, performance-driven, and refined (Dinner Under the Stars with Delta Miles)..

Dinner Under the Stars: Delta Miles Brings Cabaret Glamour to Tryst PV

The lush, ground-level courtyard at The Tryst Puerto Vallarta has officially become the neighborhood’s most intimate stage for live vocals. Every Friday night at 8:00 PM, the air fills with the timeless sounds of the Great American Songbook as Delta Miles takes the spotlight for “Dinner Under the Stars.”

A Night of Judy Garland & Live Vocals

Delta Miles (the celebrated alter ego of John Pirroni) isn’t your typical drag performer—she is a live-singing powerhouse. Best known for her uncanny and high-energy Judy Garland impersonations, Delta brings a touch of Provincetown and old-school Hollywood glamour to the heart of the Zona Romántica.

While much of the local drag scene relies on lip-syncing, Delta Miles delivers a masterclass in vocal charisma. Expect a night where the charisma of Garland meets the modern luxury of Púlpito Street, featuring everything from “Over the Rainbow” to upbeat cabaret classics that keep the courtyard buzzing.

The Experience: Al Fresco Dining & Performance

The event is designed as a seamless fusion of fine dining and theater. Set in The Tryst’s garden courtyard—complete with its heated dip pool and tropical greenery—the atmosphere is sophisticated yet relaxed.

The Food: A multi-course, seated dinner service that showcases the best of The Tryst’s upscale menu.

The Vibe: Unlike the high-volume arenas of Nuevo Vallarta, this is a boutique experience. You are close to the performer, the lighting is candlelight-meets-starlight, and the acoustics are perfectly tuned for live vocals.

The Timing: The show wraps by 11:00 PM, making it the perfect “Anchor Event” for your Friday night. You can enjoy a world-class meal and show, then walk just a few blocks to hit the dance floor at CC Slaughters or Industry right as they start peaking at midnight.

Plan Your Friday Night

Because seating in the Courtyard is very limited, reservations via OpenTable are mandatory. There is no cover charge for the show, but a seated dinner reservation is required to attend.

GAYPV Pro-Tip: If you’re a fan of live singing, this is one-third of the “Live Vocal Trifecta” in PV. Combine a Friday at The Tryst with a night at The Palm or Coco Cabaret to see the full range of vocal talent currently calling Puerto Vallarta home.

Tryst Fitness: A New Era of Wellness on Púlpito Street (Fall 2026)

While the dinner shows and pool parties celebrate the current nightlife, the most significant long-term investment in the Zona Romántica is rising just down the block. Tryst Fitness, the flagship luxury wellness brand from Tryst Hospitality, is currently under construction at Púlpito 116 (the former site of Villa Mercedes) and is on track for a Fall 2026 grand opening.

An 11,000-Square-Foot Wellness Sanctuary

Tryst Fitness is designed to be the “Social Epicenter of Health” for the LGBTQ+ community. Spanning nearly 11,000 square feet, the facility moves beyond the traditional gym model to offer a high-performance recovery experience.

• The Rooftop Lap Pool: This will be the only dedicated lap pool in Puerto Vallarta—a game-changer for swimmers who previously had to navigate the ocean or crowded hotel pools for cardio.

• The 3,000-Square-Foot Wet Area: A massive dedicated recovery zone featuring a sauna, steam room, cold plunge, and a Turkish bath (Hammam).

• Indoor-Outdoor Training: The primary training floor features floor-to-ceiling windows that open to the ocean air, blending the sophisticated equipment of a 5-star gym with the natural climate of the Pacific coast.

Investing in the Neighborhood: The Púlpito Upgrade

What sets this project apart—and what GAYPV has been monitoring closely—is the commitment to local infrastructure. As part of the construction, Tryst Hospitality is financing major street-level upgrades along Púlpito Street. This includes:

• Burying all utility cables underground for the entire block to improve views and safety.

• Leveling the sidewalks to create a seamless, pedestrian-friendly walkway from the bars to the beach.

• The Tryst Market: A 1,100-square-foot convenience store adjacent to the gym, offering healthy “grab-and-go” meals, fresh produce, and premium essentials for residents and visitors alike.

The “Chicago-to-PV” Wellness Pipeline

Just as Tryst Chicago is set to revitalize Northalsted, Tryst Fitness is the anchor that secures Puerto Vallarta’s reputation as a world-class destination for wellness-focused travelers. For those planning their Fall 2026 escape, the “Tryst Lifestyle” will offer a complete loop: a luxury stay at the hotel, a world-class workout at the gym, and “Dinner Under the Stars” to end the night.

💡 Frequently Asked Questions: Tryst Hospitality & Wellness