Old Montreal

A delightful mix of old and new, Hôtel William Gray opened in Montreal's old quarter in 2016. It's 127 rooms strong and occupies two historic townhouses plus an eight-story glass tower, with an overall vibe expertly plays up the juxtaposition. (Think rich leathers mixed with raw concrete.) A newly opened (seasonal) outdoor pool is a big hit on the second floor. Downstairs, Off the Hook, a local boutique with a cult following, is stocked with everything from exclusive Vans collaborations to wool baseball caps by Polar Skate and Arc'teryx base layers, as well as its own line of streetwear-inspired tees and beanies. The hotel's in-house restaurant, Maggie Oakes, named after the wife of Montreal's first sheriff, serves up a solid charcuterie board, grilled seasonal veggies, and, for heartier appetites, dry-aged Canadian rib eye.

Many would argue that Olive & Gourmando offers some of the best sandwiches in Old Montreal—and we agree. The O&G grilled cheese alone has us swooning with its thick caramelized onions and Gouda with house-made ketchup. The team at this charming neighborhood breakfast and lunch spot is devoted to rich dishes (think: shirred eggs and ricotta tartine), paninis, homemade soups, salads, and baked treats. There are no reservations here, so come early before the rush (or if you're in it, order a coffee and scone while you wait).

Chef Chuck Hughes's first restaurant has a supper club vibe: A dimly lit sign leads you into the dark, exposed-brick interior where the scene is always packed and a bit loud (a mix of local foodies, devoted Hughes fans, and tourists). The food is rich (the lobster poutine is a mainstay) with a heavy French influence. What tops off this popular restaurant is its impressive wine list.

The hype behind this place is legit (its owner, Chuck Hughes, has gained recognition as a TV food personality and as chef/owner of Montreal hot spot Garde Manger), as is the seasonal menu of fresh oysters, vegetable sides, and a limited but stellar mix of seafood and local meats. The food is hearty and has a French influence (note: the scallops, asparagus, and Béarnaise), which goes with the décor—dimly lit and cozy with exposed brick. A great spot for a date night.

Located in the heart of Old Montreal, this immaculate boutique has a decidedly minimalist bent. All-white shelving holds accessories by Mansur Gavriel and Commes des Garçons, while sleek racks are home to crisp, architectural pieces by Roland Mouret and Dries van Noten. The inventory is limited, showcasing only select items from each designer's current collection, which speaks to the fact that this is place to find investment pieces.

Devoted to both the performing and visual arts, this compound revolves primarily around artists from Québec, including the largest collection of pieces by abstract painter (and Canadian) Paul-Émile Borduas, who was ultimately ostracized before his death in 1960 for advocating for the separation between church and state.

Though it's primarily a guy's shop, there’s a surprising amount at Rooney that women will want to co-opt for themselves. Many of the obscure Japanese and European lines (Our Legacy, La Paz) can be easily sized down. Plus, there’s a kickass home and gifts section.

Sure, there’s the beloved, only-in-Canada department store empire Holt Renfrew, but Montreal is also home to a five-story, David Chipperfield–designed brick-and-mortar store of one of our favorite online sites, SSENSE. It offers an encyclopedic array of brands, from Balmain to Charlotte Olympia to Diemme.

Poured-concrete floors, low-slung beds, and giant windows make sense, since this boutique hotel occupies the former home of a booming import/export business from the 1900s. It’s not as cold as it sounds: The designers used plenty of gorgeous mid-century modern pieces from designers like Bertoia and Eames to warm it all up.

With dizzying views of the Saint Lawrence River and in cozy proximity to many of the city’s most celebrated spots, this nineteenth-century hotel in history-steeped Old Montreal is the total package.