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.