Most first-timers begin their explorations in Old Montreal, the warren of cobblestone streets running roughly parallel to the mighty St. Lawrence River. Rue St-Paul, one of the neighborhood’s prettiest thoroughfares, is a great starting point. To the north is the Notre-Dame-de-Bon-Secours Chapel, known as the Sailor’s Church because of its proximity to the port. Built in 1771, it features ship-shaped chandeliers, complete with billowing sails, hanging over the pews. Climb the tower to get your bearings for the rest of the day.
A short stroll south is one of Old Montreal’s architectural gems: the Bonsecours Market. Topped by a silvery dome, it’s worth a peek inside (and a quick stop for a cup of coffee and a pastry). If you want more of a meal, hold out for a few more minutes until you reach the Place Jacques-Cartier, a square lined with restaurants that spill out onto the sidewalks.
Continue down Rue St-Paul, then head west on Rue Notre Dame to reach the stunning Notre Dame Basilica. The combination of beautifully finished woodwork and the brilliant shades of blue on the floor, ceiling, and nave will make it a memorable part of your trip.
If you’re interested in Montreal’s history—and we guarantee you will be after wandering the atmospheric streets—head to the Pointe-a-Calliere, a complex built on the site of the city’s first European settlement. This isn’t some dusty old museum, though. Your visit starts with an Instagram-worthy multimedia show, then offers the chance to walk through the city’s sewers, past archaeological excavations and ancient gravestones.
When it’s time for lunch, you could eat at the museum’s glass-walled cafe, but some of the city’s best restaurants are just a short walk away. One of my favorites is Olive & Gourmando, which is half gourmet market, half busting eatery. You can’t go wrong with the homemade ricotta, served sweet at breakfast and savory at lunch.
As the sun sets, the light begins to twinkle along the walkways of the Old Port of Montreal. Far from the workaday port it once was, this waterfront area is now a scenic park beloved by locals and tourists alike. There’s plenty here to keep the whole family occupied for hours, including La Grande Roue de Montréal—a 200-foot-tall observation wheel with an unbeatable view of the river below.
For dinner, you can’t do better than Gaspar Brasserie Française, a stone-walled restaurant with dramatic arches and beamed ceilings. French brasseries are common in Montreal, but dishes like mussels simmered with white wine don’t taste as good anywhere else. In warm weather, the terrace is the place to be. For something a little less formal, there’s the laid-back Italian spot Caffe Un Po di Piu.
Fortify yourself for a trek through Mount Royal Park with a Montreal-style bagel. Locals claim they’re the best in the world—better even than New York bagels—with a denser crumb and sweeter taste. Decide for yourself at Fairmount Bagel or St-Viateur Bagel Shop, two spots with a friendly rivalry in the hip Mile End neighborhood.
How you get to your next destination depends on how much stamina you have. Many people choose to hike to the viewing area at the top of Mount Royal Park (the Olmsted Trail will get you there in about 30 minutes), but you can also take a city bus or even hail a taxi. Whichever you pick, you’ll be rewarded with sweeping views of the city skyline. While you’re up there, be sure to also check out Saint Joseph's Oratory of Mount-Royal, one of the largest domed structures in the world.
You’ve probably worked up quite an appetite by this point, so walk a few blocks north to Plateau Mont-Royal, a hip neighborhood with the restaurants to match. There are tons of choices along the main thoroughfares like Saint-Laurent Boulevard.
Don’t be put off by the line outside Schwartz’s, one of the last old-timey delis in Montreal. It moves quickly and, before you’ve even had time to peruse the menu, the staff will be ushering you to your table. The smoked meat (people compare it to pastrami) is the main reason to come here—it’s marinated in herbs and spices for 10 days, smoked overnight, and sliced to order. Piled into a sandwich with pickles and homemade slaw, it’s absolutely heavenly.
Plateau Mont-Royal is made for walking, especially because artists have covered so many of the buildings here with eye-catching murals, so go for a stroll after lunch. One of my top spots for a breather is the charming Saint Louis Square, a three-block-long park surrounded by stone houses painted in almost every shade of the rainbow.
PLATEAU MONT-ROYAL TOUR OPTIONS
When people say Montreal feels a bit like Paris, they’re probably talking about restaurants like L’Express. On a street corner in the Plateau, the bistro feels straight out of the French capital, with marble-topped tables, polished wood paneling, checkerboard tile floors, and dishes like duck confit. For something unexpected, I also recommend the Afghani food at the small but impressive Fenetre Sur Kaboul.
Parc Jean-Drapeau, spread across two islands in the Saint Lawrence River—Île Sainte-Hélèn and Île Notre-Dame—is one of Montreal’s most popular spots for outdoor recreation. Though people come here year round, it’s most appealing in the warmer months, when you can hit the hiking trails or lounge on the man-made beach. In winter, you can go ice skating on the same rink used for the 1976 Olympic Games.
In the afternoon, head back to the mainland and go for a stroll down Rue Ste-Catherine, one of the city’s major arteries.
There are many places to grab a bite here, most of them on the quirky side. One of the best is Tendresse, a bistro specializing in vegetarian and vegan dishes. The restaurant is decorated to look like a trendy version of an old-fashioned diner—and the food is equally as creative.
Rue Ste-Catherine continues past Saint-Laurent Boulevard into Downtown Montreal, an area marked by massive skyscrapers. This neighborhood is so much more than meets the eye, though, especially when it comes to what lies below street level. This is where you’ll find the Underground City—20 miles of tunnels connecting all the buildings in the area. Check it out to see how locals avoid Montreal’s brutal winter weather.
Back above ground, backtrack a bit to the Quartier de Spectacles. This outdoor entertainment district, home to the world-famous Montreal Jazz Festival, is basically one big block party. Even if you’re just breezing through, you’ll probably encounter dancing in the streets.