Entertainment District

King West Village—one of Toronto’s hipper neighborhoods full of bars, cafés, restaurants and converted warehouse lofts—is a fitting place for the Thompson, which has the same fun spirit as the blocks surrounding it. Locals love it, and you’ll often find them using the hotel as an unofficial clubhouse, whether at the Thompson Diner (a modernized version of a classic American diner), the rooftop lounge (with gorgeous views of the skyline), or Wildflower, a sleek nightlife spot for late-night revelry. The guest rooms feel more like your coolest friend’s apartment than a hotel; they’re designed by New York firm Studio Gaia with super modern furniture and little touches like heated marble bathroom floors—a nod to Toronto winters.

Toronto’s diversity of ethnic communities mean that you can probably pick any country on a map and find at least a handful of outstanding restaurant options specializing in its cuisine—including Jamaica. Chubby’s, in the city’s Fashion District, is known for its authentic jerk chicken and small bites, the best of which include salt fish fritters with a mango-lime-papaya salsa and spicy jerk chips made of plantains and taro. The interior is bright and cheerful thanks to tropical floral prints everywhere.

Although it’s technically a hotel bar (located on the ground floor of the Bisha, downtown), the feeling here is that of a private members’ club, where guests cozy up in velvet club chairs next to a roaring fire. That’s the feeling, though, not the mandate—Mister C is open to the public. The drinks are a fine complement to the intimate atmosphere. Expect a list of expensive-but-worth-it cocktails, like a premium margarita made with Don Julio 1942 tequila and the Penicillin, with Glenmorangie Original single-malt whisky, honey, lemon, and ginger.