I first became acquainted with Montreal’s unflappability while sipping on a mojito at La Distillerie, a refreshingly non-artisanal cocktail bar on Mont-Royal Avenue. This is a place where the average patron has no qualms about carrying around the lightsaber-blue beverage known as Le Patriote, a Belieber-worthy concoction made with Skyy vodka, blue curaçao and Bacardi Black Razz rum.

You see, nobody in Toronto would be seen in public holding a blue cocktail. Which got me thinking: why is that? It’s true that blue cocktails are inherently silly, but it takes a certain self-assuredness to wield one. Toronto – with its skinny jeans, Blundstones and mathematically perfect side-parts – is more hip than Montreal, but that just means we care too much about what other people think of us. Montreal, comfortable in its own skin, is far more concerned with having a good time than with appearing one way or another while doing it.

“Montreal is the French New York, and we know it,” a Montrealer friend of mine remarked. “We are the Europe of Canada and we know it. So we have that confidence.” It is a city that feels much farther away than a one-hour flight from Toronto, a city with an old town that rivals some of Europe’s prettiest, a city with a hodgepodge culture that is vaguely Parisian but distinctly its own. It is also a gourmand’s paradise, with two markets that could go toe-to-toe with Toronto’s lauded St. Lawrence (Atwater and Jean-Talon), an enviable number of internationally renowned chefs and, as Toronto coffee kingpin Sam James put it, “way higher quality everything.”

La Banquise is the go-to destination for real-deal poutine in Montreal

While Toronto only recently began to shed its prudishness (some people still call it “Toronto the Good”), Montreal’s history more or less revolves around overindulgence. Since its inception as a colonial French mission known as Ville Marie in 1642, this has been a place where people go to flirt with obesity. Centuries ago, the first French settlers to arrive in the area were amazed to find a voluptuous assortment of wild game, seafood and edible plant life, along with a native population that knew how to properly feast on all that stuff. It didn’t take long for the colonists to develop a unique cuisine that has ripened into the rotund style of Quebecois cooking we know today.

Montreal's hodgepodge culture is vaguely Parisian but distinctly its own

“The meals of the French in Canada, if I may permit myself to say so, are habitually overabundant,” observed explorer Peter Kalm in his 1749 account of life in the colony.* Consider, for a moment, poutine. At no point in time did fries need to be made fattier, saltier and more unhealthy, but Quebec did it anyway. Then there are other Quebecois classics: tourtière, the traditional pie stuffed to maximum with all manner of meats; the hot chicken sandwich, heavy on gravy and white bread; and of course, the sticky-sweet sugar-glue known as maple syrup (Quebec produces 70 per cent of the world’s supply).

The Quebecois tendency for debauchery was efficiently conveyed to me by Carlos Ferreira, founder of the glitzy Ferreira Cafe on Peel Street, as he described a meal at chef Martin Picard’s Cabane à Sucre. “It’s an experience like nothing else,” Ferreira said of the seasonal sugar shack, which dishes out heapings of corpulent Quebecois fare. “But you have to be careful. If you eat too much, you will die.” He then proceeded to stuff me to near death with European sea bass, salt cod fritters and whole shrimp bursting with umami. (Disclosure: one of my visits to Montreal was a press trip funded by Ferreira.)

Junior on the red-hot Rue Notre Dame offers highly addictive Filipino food

I haven’t yet eaten at Cabane à Sucre – I’ve bucket listed it – but I know what Ferreira means about the death-by-food thing. After eating through many of Montreal’s legacy institutions, my time spent in the city has been more or less characterized by some form of overconsumption-related discomfort. I now know that Quebecois food is so over-the-top good that it’s probably best to consume only a quarter of what you think you’ll have the capacity to eat.

I learned this lesson the hard way on Rue Notre Dame, in and around Little Burgundy, which in recent years has become the culinary heart and soul of Montreal. Once a wasteland, this neighbourhood is now like Ossington on steroids thanks to chefs David McMillan and Fred Morin, who pioneered the area’s transformation when they opened Joe Beef there in 2005.

Now it’s impossible to walk 10 feet without strolling past a slick new wine bar, food shop or restaurant, such as Satay Brothers (which serves some of the best Southeast Asian food in the city), Junior (which makes a crispy- good sisig, a sizzling sweet-and-sour Filipino dish made from pork offal) or Boucherie Grinder (which has to be the most artisanal of artisanal meat shops in the city).

Joe Beef, meanwhile, has become a near-universal starting point for exploring food and drink in Montreal, and I went in unprepared for the gluttony that was about to transpire. After tearing through a seafood platter laden with oysters, shrimp, lobster and deliriously funky sea urchin from Quebec’s Gaspé region, I proceeded to stuff myself even further with deep-fried softshell crab, tartare and ruby-red duck breast. Although I planned to do other stuff afterward, the meal did me in. I spent the rest of the night in bed, unable to move, half regretting that I had somehow managed to eat so much and half proud of it.

By the time I made it to Au Pied de Cochon, another Montreal institution, I had a plan of attack: no eating for eight hours beforehand, and no bread at the restaurant. These are things you need to consider when going to a foie-gras-on-everything place. And Au Pied really does put a stupid amount of foie gras into just about everything: the poutine, the duck-in-a-can and the nigiri (this, with its vinegared rice and dangerously addictive maple-soy sauce, is a highlight).

Au Pied Du Cochon puts a stupid amount of foie gras in everything

I can’t really think of a better way to spend an evening than by sipping on Calvados and pushing yet another piece of foie into your mouth. The best seats here are at the bar, where you can watch all the zaniness of a pirate-ship kitchen unfold as the cooks speak to each other in that magical (and truly Canadian) hybrid tongue known colloquially as “Franglais.” I survived that meal without spending the night sweating it out in the fetal position – but only barely.

In a city partially defined by its love of poutine, the locals have a true and undying affection for La Banquise on Rue Rachel. It’s so universally acknowledged as the place for poutine that to praise it out loud will elicit a smattering of “no shit, Sherlock” eye-rolls. This 24-hour poutinerie has been open since 1968, and to this day it needs bouncers to deal with the lineups.

La Banquise makes its poutine with red potatoes – which are slightly sweeter than russet potatoes – that are twice-fried for crispiness. I am convinced that this salty-savoury-sweet combination cannot be improved upon and should receive some sort of governmental designation to preserve authenticity, like Neapolitan pizza. I got mine with hot dogs added (because why not?).

The excellent Jean-Talon Market

Thankfully, Montreal is also good at morning time debauchery recovery. The city isn’t as high on third-wave coffee as Toronto is, perhaps because of its European sensibility, but good coffee abounds. Cafe Myriade proudly proclaims that it is “not a third-wave coffee shop,” but it makes a good espresso nonetheless. On the bohemian Mont-Royal Avenue – my favourite neighbourhood in the city – La Distributrice provides caffeine to-go out of a “café” that’s the size of a closet. It’s worth a visit for the novelty or the coffee or both.

The best espresso I had was at Larry’s, a wine bar in Mile End that draws in young, good-looking gastronomes by the half-dozen. It’s rare to find great coffee at a place that doesn’t specialize in it, which makes Larry’s a bit of an enigma. The cocktails are good, too: the Réunion – made with white port, lime juice and grapefruit juice – is a fine way to recalibrate after a night about town. As is the sea urchin on bread with kohlrabi, because when in Rome, eat sea urchin before noon.

Rue Notre Dame is now the city's culinary heart and soul

It should be noted here that Montreal has prime access to seafood due to its proximity to the St. Lawrence river and the ocean. There are many restaurants in which to indulge, but for a slightly out-of-the-way spot where the lineups aren’t likely to include a single tourist, Lucille’s Oyster Dive on Monkland Avenue is worth the trek. The oysters here are some of the most flawlessly shucked I’ve seen, and there is also a beef dry-aging room in case your date isn’t obsessed with seafood.

As I wandered Montreal’s streets – which, due to a history of bylaws, are less crammed with skyscrapers than one might expect – I got to thinking about Toronto’s tastemakers and how they would fare here. Which is pretty well, if Agrikol is any indication. This Haitian rum bar from the Black Hoof’s Jen Agg exudes the timeworn prettiness of a Caribbean old town: its aesthetic is part Jacmel – an arts and culture epicentre in Haiti – and part New Orleans. Agg, a master of ambience, has created a magical place that throbs with energy (and high-volume kompa) on even a midweek night. The food is soulful and the rum is some of the best you’ll ever taste (Venezuela’s Diplomatico can induce goosebumps).

Upon returning home from a Montreal jaunt, I had the audacity to mention to a friend of mine that it’s a city I kind of enjoy. “Of course you like it,” he said, perturbed that I’d say something so obvious. “It’s like going to Europe without going to Europe.” He has a point. But I doubt even the French are comfortable enough to flaunt a sugary, neon-blue cocktail.

* For a meticulous rundown of the history of Quebecois cuisine, check out “Another World” by Canadian writer Adam Leith Gollner in issue 11 of Lucky Peach.