While staying downtown would not be my first recommendation when you’re in Montreal (the Plateau and Little Burgundy are where it’s at!), it does have its benefits. Mainly, a very central location in the heart of the city, and lots of hotel options.

Where to Sleep

If budget allows, the Ritz and the Four Seasons are right around the corner from each other downtown. If not, I’ve stayed at a few spots downtown that worked just fine.

Hotel Vogue: This dog-friendly hotel is where Reggie spent his first night in Montreal back in 2018 when the temps dropped to -20 F. The hotel provided an in-room dogsitter who took Reggie out for walks in the heated parking garage because he refused to go outside. There’s a tiny bar off the lobby that’s worth checking out.

Chez Swann: Funky design that borders on the garish with a French restaurant.

Eat like it’s an Olympic Sport

Sushi Hidden Fish: Stylish spot for super fresh fish and the best sashimi and sake. Try any of the nigiri with wagyu for melt-in-your-mouth deliciousness.

Boustan: A local chain that serves the absolute best falafel pita. I was a regular fixture at the original Crescent Street location most nights around 3:30am in college.

Weinstein & Gavino’s: There’s this weird thing that happened to me when I was living in Montreal for five years. Surrounded by some of the most diverse, interesting and authentic food you can find in the world, I found myself craving the suburban familiarity of an Olive Garden. One weekend in college, my friends and I even drove over an hour into Vermont to actually go to an Olive Garden. Can’t believe I’m admitting that. Nevertheless, if you want a very predictable – but good! – Italian-American type meal that’s leaps and bounds above Olive Garden, Weinstein & Gavino’s will scratch that itch.

Eggspectations: A local brunch chain with a location on Maisonneuve that was across the street from where I lived, so naturally was where I spent many a weekend.

Drink Like a Local

Cloakroom: This 25-seat cocktail bar on de la Montagne is a regular on the “best of” lists and — fun fact — next to the apartment I lived in for the last two years I was at McGill.

Peel Pub: OK so I don’t think you’d catch a real Montrealer inside Peel Pub, but it’s on my list despite this. The basement location of the early 2000s is no more, but don’t let the slick, multi-level new location fool you. It’s still a dirty dive/dump of a bar that specializes in pitchers of cocktails, fountains of beer, $1 shooters and getting rip-roaring wasted with American teenagers.

Sir Winston’s: This Crescent Street bar was a favorite of mine in college.

Shopping

Mackage: It can be a humbling experience to first visit Montreal in the winter and think you have to dress like it’s a ski day to stay warm. Montrealers do winter coats really really well and local brand Mackage is my favorite of the bunch. Tailored wool coats, ski puffers, fur-trims… if you want to stay toasty warm in -20 degrees while simultaneously looking chic, head to Mackage on Saint-Catherine.

Holt Renfrew Ogilvy: RIP to the original Holt Renfrew on the corner of Sherbrooke and de la Montagne, where I abused my credit card privileges after learning about designer denim in the year 2001. This new megastore is an Ogilvy-Holt Renfrew combo so it’s got the necessities of a Macy’s along with high-end designer boutiques.

Simon’s: A majority of my college wardrobe came from Simon’s, which I describe as a mix between H&M and Primark.

Hudson’s Bay: A Canadian institution going back hundreds of years when they used to trade fur.

Excursion-Worthy

Curling: It’s funner with a group, but if you’re alone or just a twosome, taking a curling lesson is a hilarious way of spending an afternoon. Bring warm and comfortable clothing since you’ll be on ice (it’s inside but still gets cold). You can track down a lesson on Airbnb Experiences; the most popular spot is about 15 mins west of downtown by car.

Montreal Tips & Tricks

Parking: Street parking is fairly easy to find; just pay attention to the signs for weekly street cleaning. Download the P$ app to pay by phone. During the winter months, they will tow your car in order to plow. But since it’s Canada and everyone/everything is nice, they just tow it a few streets over and don’t give you a ticket.

Reservations: Download the DINR app, which gives you access to last-minute table availability at some of the city’s best spots like Vin Papillon, Liverpool House, Garde Manger, Caffe Un Po Di Piu and more.

Alcohol & Cannabis: These are federally controlled so can only be purchased at province-run stores such as the SAQ (beer, wine, booze) and the SQDC (cannabis). And there’s no such thing as gummies in Canada, but they do sell cannabis pills, seltzers and snacks. You can buy beer and cheap wine at most deps (short for depanneur, like a convenience store), including chain ones like Couche-Tard.

BYOB: There are a ton of BYOB restaurants in Montreal, including a cluster on Duluth Avenue in the Plateau where almost every cuisine is represented. In college, my favorite was L’Academie but the St. Laurent location has since closed and the one on Crescent just isn’t the same.