One of my favorite ways to get my bearings in a new city is through a walk or bike ride. In Montreal, I opted for a bike tour with Shea Mayer, founder of Fitz Montreal Bike Tours. These guys organize the best bike and walking tours, year-round. On our ride, we explored Montreal’s unique laneways. Once used as service rows for things like ice delivery and garbage collection, many of these narrow corridors are now hidden gems, often off-limits to cars, and filled with gardens, kids playing tag and art. It’s just one of the many ways Montreal offers unexpected bursts of creativity and community.

1950s Montreal experienced a huge influx of Italians. Today, Little Italy continues to be one of the most charming and vibrant neighborhoods in the city. Restaurateur and third generation Italian-Canadian Stefano Faita showed me around. I adore grocery shopping on any trip (yes, seriously) and Milano Fruiterie was everything I wanted from an Italian grocery store and more.

Open since 1954, you’ll find Italian imports here that aren’t available anywhere else in town. Their cured meats are some of the best in town—order a smattering of items and enjoy in a nearby park (or if it’s cold, maybe even in your hotel room!). Plenty of Italian grandmas shop here daily, so you know it’s good!

In all my travels, I’ve never ever been to a place quite like Dante.  Open since 1954, this corner store specializes in, well, just about everything. It’s part hardware store, part kitchen shop, and a bona fide gun shop. Where else in the world can you buy a peppermill and a shotgun in the same place (and big box stores don’t count!). Still family owned, this place has to be seen to be believed.

There’s nothing like a enjoying a cup of coffee in a place that’s been around forever. In Little Italy, that iconic spot is Café Italia. You won’t find a mustachioed barista in suspenders here—it’s as old school as it gets. Owned by the same family since opening in 1956, any renovation has been intentionally reminiscent of the original. Who cares if they could afford real wood floors, they’ve instead replaced the old stuff with laminate— to keep it looking as original as possible. Order a cappuccino and mingle with the locals. This is where they hang.

Named after the beloved figure who stole from the rich and gave to the poor (that would be Robin Hood), Robin des Bois strives to serve incredible food while concurrently serving its community. Founded by Judy Servay, Robin des Bois is one of the only restaurants of its kind. Whatever excess money the restaurant makes is funneled right back into the community. It’s an easy way to contribute to charities working to make Montreal a better place for all. Originally located on St. Laurent Blvd., the restaurant has since relocated to Avenue du Parc-La Fontaine in Le Plateau-Mont-Royal after a fire in 2021 and luckily is still thriving.

What’s more, the globally inspired menu is delicious. Japanese-inspired rice bowls, yummy poutine, and Nordic-style smoked salmon sandwiches with salty lemon confit, sour cream, and dill are just a handful of options.

Did you know Montreal is the unofficial headquarters of the modern day circus—or cirque, if you want to use the correct terminology. I had the great pleasure of joining cirque choreographer Anthony Venisse in bringing circus performers to the city streets during the 11-day Montreal Cirque festival. Held every July, you’ll find troupes performing all over Montreal.

However, no matter when you visit this great city, the circus is always in town. Seven Fingers (or Les 7 Doigts),  Cirque Eloize and Cirque du Soleil all typically have shows ongoing in Montreal, so it’s worth checking the local listings to see if you can catch one.