I ranked Canada's biggest cities from least to most overrated — This will burst some bubbles

#4. Montreal

The hype: Europe without leaving North America.

The expectation: Montreal is usually sold to the rest of Canada as our little slice of Europe: cobblestone streets, French architecture, tiny cafés and people smoking cigarettes attractively outside of bars. You're supposed to visit, eat a bagel, walk around Old Montreal and briefly forget you're still in Canada.

The reality: Calling Montreal "Europe without leaving North America" almost undersells it, to me. Montreal doesn't feel like a Canadian city cosplaying as Paris. It feels completely like itself — and, in my opinion, it's the best city in Canada.

Recently, a weird number of Montrealers have come into my orbit in the U.S., and every time we discover the connection, we eventually arrive at the same conclusion: "Yeah, Montreal is the best city." There's almost nothing to debate.

It has the food and architecture people promise, but it also has something most Canadian cities struggle to manufacture: an actual personality. Even if sometimes that personality is a bit b*tchy.

There's nightlife, fashion, history, art and interesting people who don't all appear to work in real estate (*cough cough* Toronto). Even its inconveniences — the brutal winters, endless construction and perpetual language politics — feel specific to the place.

Montreal lives up to its reputation, but I still think it's quietly underhyped. People talk about it as a charming place to visit. They should talk about it as one of the genuinely great cities in North America.

#3. Calgary

The hype: "The Texas of Canada".

The expectation: Calgary's reputation is basically cowboys, oil money, pickup trucks and the Stampede. It's treated as a place where everyone owns boots, eats steak and becomes briefly intolerable every July. Unlike Vancouver or Toronto, nobody seems particularly invested in convincing the rest of the world that Calgary is a glamorous, world-class destination.

The reality: I'm ranking Calgary this low on the overrated scale for one simple reason: I'm not sure it gets enough hype to be overrated. I have never met someone abroad who gasped when I mentioned Calgary or told me it was at the top of their travel bucket list.

And honestly, that works in Calgary's favour. It's clean, modern, close to the Rockies and more cosmopolitan than its cowboy reputation suggests. It has the confidence of a city that knows exactly what it is and isn't constantly demanding applause for it.

Calgary may not be Canada's most exciting city, but it also never promised to be. You arrive expecting corporate offices and cowboy hats, and you get corporate offices and cowboy hats — plus a surprisingly pleasant city underneath.

In a ranking based on the gap between reputation and reality, Calgary benefits enormously from managing expectations.

#2. Toronto

The hype: "The New York of Canada".

The expectation: Toronto is Canada's biggest city, so naturally, it's sold as our centre of everything: business, culture, fashion, food and entertainment. It has skyscrapers, celebrities, professional sports teams and Drake continuously reminding the world that he is from there. The expectation is that Toronto has the scale, diversity and energy of a genuinely global city.

The reality: Toronto is a good city. In fact, it might be a great one — but every time it calls itself "Canada's New York," it sets itself up for failure.

It has incredible food, ambitious people, and more going on than almost anywhere else in Canada. But it also has the exhausting energy of a city trying very hard to prove that it matters. Toronto doesn't just want to be enjoyed; it wants to be taken seriously. It wants you to know it has money, celebrities and culture. (The celebrities are Drake, and the culture is Cactus Club).

And I think that insecurity, paired with street style that's exclusively Aritzia, is what makes it feel overrated. Toronto is at its best when it stops auditioning to be an international capital and simply acts like Toronto.

Unfortunately, the city seems to believe being Canada's largest automatically makes it Canada's best 😬.

#1. Vancouver (Canada's most overrated city)

The hype: "The most beautiful city in the world."

Expectation: I think it's safe to say Montreal and Vancouver duke it out for the title of Canada's best city. Sorry, Toronto — despite Drake's best efforts, you are simply not in the conversation the way you think you are.

Vancouver's reputation absolutely precedes it. I would know — I'm a born-and-raised Vancouverite who has lived in the U.S. for the past decade. Whenever I tell someone where I'm from, I get rave reviews. People who have visited Vancouver seem to love it, while those who haven't talk about it as if it's some misty coastal paradise they need to see before they die.

Reality: Vancouver may have one of the most beautiful settings in the world, but that doesn't make it one of the most beautiful cities. The mountains are beautiful. The ocean is beautiful. The trees are beautiful. But Vancouver itself has spent decades bulldozing its character and replacing it with the ugliest green-glass towers imaginable.

Maybe I take the scenery for granted, but the way people talk about Vancouver, you'd think it was the Amalfi Coast. Guys, it's Seattle+.

I think Vancouver suffers from "a cut above" syndrome. It's cleaner than most cities, prettier than most cities and has better weather than almost anywhere else in Canada. The food is good, the mountains are close, and the ocean is right there. It is reliably above average.

But above average isn't the same as great. Vancouver does many things reasonably well, but it doesn't offer the culture, nightlife, architecture, energy, or distinct personality of a truly world-class city (which is claims to be). Because it's a cut above much of Canada, people talk about it as if it's a cut above everywhere. It isn't.

Except for the sushi. That sh*t is fire.