Part of Little Italy since 1956, Caffè Italia is one of those rare places that has never really needed to reinvent itself—the Serri family have kept it exactly as it should be, a second home for generations of Italo-Montréalers gathered over espresso and pastries.

"I've been going there for almost 40 years. I consider it my place. I always had a special bond with the Italian community, and I knew the family that had Caffè Italia before—so you kind of feel like you're still part of the community."

In the shell of a former bank just off Phillips Square, Bar Phillips is the newest project from the Jatoba team—part sushi bar, part cocktail lounge, part downtown escape, with mid-century design and pricing that stays generous.

"I like these kinds of hidden places. It's very classy, the food is fantastic, the service is great. It's a nice hangout place to have a good meal—and these days it's one of my favourites."

Founded in 1998, Stereo is less a club than an institution—a no-frills sanctuary for house and techno purists, with a world-class sound system and a crowd that regularly stays locked in until well past sunrise.

"The go-to places for me are related to music. I'm very much into electronic music, and Stereo is really where I can decompress. It's therapeutic. I'm dead tired tonight but I'm still going out—that's what it does to you."

A vinyl-only listening bar in a Chinatown basement beneath the Japanese restaurant Fleurs & Cadeaux, Sans Soleil starts evenings with sake and sushi before transitioning into a standing-room-only club that goes late.

"When I need a break in production mode, that's where I escape. We'll grab a bite at Fleurs et Cadeaux upstairs and then move downstairs. It's a fantastic place."

Since opening in a Chinatown basement in 2014, Mal Nécessaire has moved to Saint-Alexandre Street and refined its tropical tiki formula—meticulously crafted cocktails, velvet banquettes, subdued lighting, DJ-curated music—without losing any of its original energy. Still Life, nearby, is cut from the same cloth.

"When I have visitors in Old Montreal, it's usually the first stop. There's nothing else quite like it in Montreal."

Sitting four floors above Place Jacques-Cartier at the William Gray Hotel, Perché swaps cobblestone charm for a California-inflected rooftop escape—poké bowls, dumplings, and a globetrotting wine list, with no reservations after 4 p.m.

"It's less known than the William Gray terrasse, but the view is just as fantastic."

Since 1964, the MAC has been Canada's leading institution for contemporary art—nearly 8,000 works, immersive exhibitions, and a programming instinct that keeps one eye firmly on what's happening now.

"The curation is fantastic—very inspirational for me. At Oasis, we always try to choose topics that are in the zeitgeist right now, and the MAC has always been a source of inspiration for that."

Spread across roughly one square kilometre at the heart of downtown, the Quartier des spectacles packs in more than 30 performance venues, dozens of annual festivals, and eight public squares whose projection surfaces and lighting networks turn the neighbourhood into something else entirely after dark.

"Before a show, I'd send someone to wander around the Quartier des spectacles—along Sainte-Catherine, the projections, the skating rink with the interactive features. It puts your mind into an artistic spirit. It prepares your mindset."

One of Montreal's great urban reinventions: 192 hectares of former landfill in Saint-Michel transformed into trails, meadows, and cross-country ski paths, dotted with white biogas-collecting spheres that give the landscape a genuinely otherworldly quality.

"What surprises me is how many people still don't know that park exists. There are certain parts where you feel like you're in a Star Wars movie. I've biked all the way to La Visitation from there."

"Sometimes we just go hang out there to take in the vibe. It's a good spot."

First laid out in 1693 and surrounded by some of the city's most significant architecture—Notre-Dame Basilica, the Saint-Sulpice Seminary, the Bank of Montreal's historic headquarters—Place d'Armes is as compact a lesson in Montreal's history as you'll find anywhere.

Perched on the eastern tip of Cité du Havre with panoramic views of the Old Port, the downtown skyline, and the Jacques Cartier Bridge, Parc Dieppe is an underrated escape that most people only discover by accident—or by following someone who already knows.

"During the day it's really nice, and at night you have the city and the river as a backdrop. It's a fantastic place. Fair warning: the landscape slopes down toward the water, so if you bring kids and a soccer ball, you will lose it."

"The coffee is really good and it's a good place to disconnect."

Named after a Jacques Derrida concept by its philosophically inclined founder Daniel Alvarez, Café Différance (or ‘diff.’) sits on Avenue Viger at the edge of Old Montreal—simple, warm, rotating Canadian roasters, pastries from Hof Kelsten, and a quiet remove from the neighbourhood's busier corridors.

"For lunch within walking distance of the Palais, Fiorellino is where I go."

From the Buonanotte Group, Fiorellino brought an Italian snack bar format to rue De la Gauchetière in 2016—wood-fired pizzas, house-made pastas, a mid-century interior that lands somewhere between neighbourhood trattoria and lively downtown bar.

"For dinner after a big premiere night in Old Montreal, Mama C. The food is fantastic."

Named after the founders' mother, Mama C moves through the day from Mediterranean café to aperitivo spot to a dinner anchored by wood-charcoal grilling—seafood, meat, and vegetables finished simply with herbs, citrus, and olive oil.

"It's one place I'll still go physically. They have a decent approach to style—I always find these little accessories that make sense."

Founded in Quebec City in 1840 and still family-owned five generations later, Simons' downtown Montreal flagship on Sainte-Catherine has long blended retail with cultural experience, anchored by a suspended Guido Molinari sculpture that sets the tone the moment you walk in.

"I went last year during MUTEK to see a performance there. I actually consider that a hidden gem in Montreal."

Reimagined by Lemay and nestled in Parc La Fontaine, this 2,500-seat open-air amphitheatre hosts a summer lineup that spans live music, dance, circus, theatre, and film—most of it free.