Photograph by Arpad Benedek, Getty Images
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Streetcars travel down King Street in downtown Toronto.
Photograph by Arpad Benedek, Getty Images

Toronto hides its charms under a practical façade. "If it were a wine, it would not be fruit forward," says Canadian author Andrew Pyper. "You need to pour it into a decanter and let it sit for an hour." Indeed, this "wine" is reaching its peak now. The capital of Ontario is experiencing a building boom (there are more towers going up than in Mexico City or New York), and its waterfront revitalization is the largest urban development project on the continent. Visit the ever widening strip of galleries and shops along Queen Street West, sample the Latin flavors of the latest wave of immigrants to populate Kensington Market, or see how wise planning revived the Distillery District.

When to Go: May for the CONTACT Photography Festival, August for the Caribana parade, September for the Toronto International Film Festival, and January for prix fixe deals during the food festival Winterlicious.

Where to Stay: Just blocks from each other, both the Gladstone and the Drake were reborn from down-at-the-heel obscurity. The Gladstone may be slightly more artsy, a result of trying to keep it accessible to the artists who still frequented it in its dustier days, while the Drake—with a popular rooftop bar—comes off as hipper.

How to Get Around: The 15.4-mile-long 501 Queen streetcar route runs from working-class Mimico in the west to the tony Beaches in the east, passing the neighborhoods below. On weekends, the Toronto Transit Commission day pass allows unlimited travel for two adults and four children.

Helpful Links: Even better than the TTC's official site is the Rocket Man app, which tracks your streetcar or bus with GPS. BlogTO lists several more transit apps, and is a great resource itself. National Geographic's Guide to Toronto

Fun Fact: Torontonians collectively speak over 140 languages. In fact, one in three speaks a third language (not English or French) at home.

Queen Street West

What to Do: Walk west from Victorian Old City Hall to swinging '60s New City Hall (which has a rink in the winter). Torontonians actually favor West Queen West, where retail chains give way to independent stores such as Gaspard, with its emphasis on quality fabric and fit, not trends. "West Queen West is for the people who live in the city," Pyper says, where things "get winnowed down from the mainstream to more specialized for the browser."

Where to Eat or Drink: Banh Mi Boys do a nontraditional take on Vietnamese sandwiches, subbing in duck confit, for example. Oyster Boy serves a selection of Canadian and American oysters, best accompanied by a Caesar, Canada's answer to the Bloody Mary.

What to Buy: Type emphasizes independent Canadian literature, with a great kids' section too. Spectacle's architect-chic glasses are pricey but not eye gouging. At Magic Pony, pick up a silly plastic toy or a clever artist's print.

Kensington Market

What to Do: Browse the vintage clothing shops, the last legacy of the shmata businesses (tailors, dressmakers, and furriers) that once characterized the immigrant Jewish neighborhood. Debate the merits of the dragons lining the median on Spadina Avenue. Get a quick haircut from the tattooed, neatly cropped men at the Crows Nest barbershop.

Where to Eat or Drink: Have a smoked marlin taco at Seven Lives. Ignore the inauspicious downstairs entrance and try the liang pi cold noodles at Chinese Traditional Bun. Sanagan's Meat Locker likes to get creative with their takeaway sandwich specials, such as the bacon roll with mushroom frittata, arugula, and spicy mayonnaise. Round out the meal with a locally brewed beer in bike-themed Handlebar.

What to Buy: Check out mid-century modern vintage clothing from Bungalow. A few doors away, pick up silk-screened T-shirts with views of Kensington Market and other iconic Toronto scenes at Model Citizen.

Distillery District

What to Do: Visit artist studios in what was once the largest distillery in the world. Get rush tickets to Soulpepper Theatre Company. Picnic on the sand under the pink umbrellas by the granite rocks and maple trees at man-made Sugar Beach.

Where to Eat or Drink: Les Louises, in the foyer of the Young Centre for Performing Arts, serves simple but fresh fare that changes daily (chicken with brie, pear, and kale sandwiches, roasted veggie and quinoa salads, homemade cookies and brownies) in a grand space, with a fireplace and communal tables. Order the beer suite at the warehouse-style Mill Street Brew Pub.

What to Buy: Handmade on the premises, Hoi Bo's unadorned bags have carefully engineered interiors. Distill Gallery features clothes and home décor designed and made in Canada, including Avril Loreti's pillows and towels decorated with old-school hockey players (sans helmets).

Nyka Alexander was born in Ottawa, raised in Montreal, and lives in Toronto when she isn't becoming more Canadian by traveling abroad.