Having worked our way through the Shangri-La's restorative full English breakfast, Max and I head a few blocks north to the Art Gallery of Ontario, which spans the centuries and is spiced with the kind of woke wit that allows signs to be translated casually from English into Anishinaabemowin, an indigenous tongue. The museum itself is a work of art, especially Frank Gehry's woozy spiral staircase in the mammoth central atrium.

In a dark room containing Hank Willis Thomas's retro-reflective prints, flash photography is not only encouraged but necessary: the images can be seen only in the brief burst of light. Sandra Meigs and Christopher Butterfield's Room for Mystics is a romper room of oversize primary colors. Esmaa Mohamoud's ball gowns made from Vince Carter basketball jerseys are deliciously impish and structurally flawless. And there is a haunting beauty in standing inches from Shauntay Grant's great-grandmother's handmade quilt as Grant reads poetry through speakers tucked behind the fabric: “Show me secret ways of feeding from forest feasts, flower dumplings, and blueberry stew. I want to know potatoes, pan-fried pain too much on the belly. Grandmother, teach me."

The poem is inspiring, but also mouthwatering, so we head off to Dim Sum King, a large restaurant on the third floor of a nondescript building in nearby Chinatown. On the way, we take a detour through Grange Park, which reopened last year after a multimillion-dollar revitalization, part of which involved the introduction of a Henry Moore sculpture, Large Two Forms, which was moved here from another part of the city—a decision that caused a stir among local art lovers.

The museum's spiral staircase

Dim Sum King is a low-key spot, yet the walls are covered with photos of celebrities who have eaten here. Prime Minister Justin Trudeau appears to be a regular, and within moments of sitting down I can see why: Carts of wonderful treats are wheeled up to our table, including pillows of steamed buns and dumplings that are the culinary equivalent of a spa treatment. We burn the buns off by walking to the historic Distillery District, which is built around a landmarked 19th-century brick distillery and is now a magnet for artists, foodies, and sundry craftsfolk.

It's incredible how open these people are to discussing their work, even as they go about making it. At the Sarah Phelps Art Gallery, the eponymous painter gives Max and me a guided tour of nearly every work in the space—the inspiration, the process, the emotion. At the Thompson Landry Gallery, we view the hypnotic oil paintings of Ognian Zekoff, which focus almost entirely on hands, along with the folkloric Technicolor prints of Anishinaabe artist Norval Morrisseau. At Soma Chocolatier, we buy chocolate birch branches stuffed with raspberry jam and nougat, as gifts for folks back home. Tastier than olive branches, eh?

"The Art Gallery of Ontario itself is a work of art, especially Frank Gehry's woozy spiral staircase in the mammoth central atrium."

North of here, on the fringes of the funky Annex district, we come across Snakes & Lattes, which offers coffee and board games in a space with a distinct living-room vibe. So much of this city is homey. For a true taste of Toronto's stylishness, though, you have to go a block west to Bar Raval, which is largely hidden from the outside world, identifiable only by a plain wood door. Inside is a Hobbit house of swirling dark wood, Gaudí-style, where Spanish tapas are served. Think of it as the home of Bilbao Baggins.

The Distillery District's trademark cobblestone streets

While sipping the mole-infused cocktail Glass Case of Emotion and the apricot and celery Into the Sun, we eye passing platters of mushroom towers and tuna pickle gildas and just the sheer transportative splendor of the place. All the people here, Max and me included, seem to be discovering fantasy versions of themselves—a bit cooler, a bit more adventurous. The overall effect is the opposite of a singles bar: It hums with the communal pulse of a house party.

From here, we head to DaiLo, a modern Asian bistro inspired by chef Nick Liu's family recipes. An amuse-bouche of green tomatoes comes from Liu's own backyard, pickled kimchi-style then tempura-fried. His pork and shrimp dumplings in XO sauce are made with his grandmother's recipe. There are also a few wild novelties, such as a fantastic Big Mac bao (in which the fast-food classic is reimagined with 90-day dry-aged ribeye), tofu in KFC batter, Vietnamese tiramisu, and sake sorbets.

The Into The Sun cocktail at Bar Raval

While eating a crunchy jellyfish slaw, Max (a molecular biologist) remarks to our Brazilian waiter that jellyfish are the least-evolved creatures that sleep—“Well, the lowest metazoan with a circadian rhythm that manifests a sleep-like behavior." The waiter is unfazed, chipping in with a factoid of his own: “And do you know that there are more types of jellyfish than any other type of creature? It's the most varied creature."

Toronto after dark is oddly mischievous, as if the city is playing dress-up with the cloak of night, everyone running around in the glow of a school recess. The city, somehow, has gamified adulthood. After a while, you stop being surprised by the sight of someone walking down the street with a stroller filled with beer, or riding a unicycle, or playing a ukulele. We see all three of these things through our cab window while on our way to House of VR, where virtual reality playpens are rented in half-hour blocks.

I get my virtual legs in a world made up of Vincent van Gogh paintings. Goggles on, there I am in 1888's The Night Café. Down the hall, past a vase of sunflowers, is Marguerite Gachet at the piano. And in a nearby armchair is van Gogh himself. We listen to an impromptu concert before the artist gets up and walks over to a window. I join him. Outside is his Café Terrace at Night. I suppose we are in Arles. Something else has van Gogh's attention, so I poke my head out the window and follow his gaze skyward. There, swirling to the point of dancing, is the giddy firmament of The Starry Night.

During the cab ride home—I'm already thinking of the hotel in these terms—our driver tells us that everyone in Toronto has a nickname, even though he doesn't. He dubs us Richie Rich and Maximilian, but then changes his mind. “That's too easy," he says. “But they're both about money. So maybe one of you could be Loonie, like the $1 coin, and the other could be Toonie, like the $2 coin, and then when you show up people could call you the Loonie Toons. Or, like, it's Loonie Toons time. I could see that with you two."

Day 3

Tasting Canada's history and ultra-diverse future

Back in the city proper, we do a bit of shopping on bustling Dundas Street—primarily window shopping, since we've spent most of our disposable income on chocolate—but can't resist dipping into OVO, the owl-branded clothing store made famous by the rapper Drake. It's minimalist but fanciful (if you fancy $100 khaki-colored sweatpants). I end up popping into a no-name gift shop in Chinatown to buy some allegedly lucky coins. Toronto makes you believe in good luck, even if it doesn't make you believe in sweatpants.

A hexagonal staircase at the Aga Khan Museum

There is a giddy timelessness to this city's magic, and there's no better place to experience that spirit than Boralia, a restaurant whose menu is derived from the cuisine of indigenous people and early settlers. Keeping with this concept, many dishes come with date stamps that refer to the year the recipe was devised. We have deviled Chinese tea eggs (1855) marinated in soy sauce, Chinese wine, black tea, and five spice powder served with pork sausage and chives on top; mussels smoked in pine needles and pine ash butter (1605); and tavern keeper's duck (1851) with hibiscus-wrapped sausage, Arctic cranberries, and birch syrup. The star is a simple pigeon pie (1611), a testament to the idea that less is more. Luckily, we save just enough room for a bird's-nest pudding of fried butterscotch custard (1894).

"The ancient dish is inscribed with Arabic text that could stand as Toronto's motto:'Generosity is the disposition of the dwellers of Paradise.'"

I ask that my grandmother and pastor and any future employers not read this next part, but we end our last night in Toronto with a bar crawl, during which we sample the Haitian-inspired tipples of Rhum Corner, the low-key Hoof Cocktail Bar's Manhattan, and the draft beers at Otto's Bierhalle (where I highly recommend you push the giant red button in the bathroom). One fellow barhopper insists that we visit the speakeasy-ish Civil Liberties, adding, “Look for the pineapples." On Bloor Street, we pass by Christie Pits Park (home to the Erratic Boulder, a boulder with a plaque that reads “Erratic Boulder"). Then we see it: an awning peppered with pineapples.

Civil Liberties is so confident in its craft that it has no menu. Every drink is tailor-made. The bartender promises she can give me any flavor I want, so I ask for a drink that tastes like Toronto. It turns out there's an actual cocktail called the Toronto—a Fernet-infused play on the Manhattan. As I sip it, the band wraps up a song about mustaches, then asks the audience to suggest words that might inspire an improvised number. “It's our last night in Toronto!" I yell, a bit too—how to put it?—yell-y. Duly prompted, the band delivers a rousing ballad titled “Last Night in Toronto":

I want to let you run
It don't matter where we go
It don't matter where we go
Everybody needs
somebody to love
When it's your last
night in Toronto
It's our last night
in Toronto
Won't we have fun
It's our last night
in Toronto
And it's only just begun

As we leave, I look back wistfully and catch the banner above the bar's entrance. In another century, it could've been emblazoned across the city's gates: “This must be the place."