Travel + Leisure is exploring North America one three-day weekend at a time. Here’s what to do during a short trip to North America's fourth-largest city, Toronto. 

By Kimberly Lyn
November 21, 2019
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Canada’s largest city is known for its diversity – boasting a population of 2.9 million residents who represent 200 ethnic groups and speak more than 140 languages. International cultures are celebrated throughout the city in its restaurants, shops, and museums — and this is just one of many reasons Toronto is a great city to visit. To experience the best of Toronto, this three-day travel guide navigates you from west to east with points of interest both on and off the beaten path. We recommend tailoring your itinerary to the season — in the summer, plan for long outdoor strolls as the city comes alive with innumerable cultural festivals and events. In the winter, you are likely to spend more time indoors – but don't worry, there are plenty of activities in "The Six" to keep you entertained. Just make sure to dress warmly; Toronto winters are notoriously cold and snowy. 

Day One

Start with breakfast at the Drake Hotel, and then stroll through West Queen West, named one of the coolest neighborhoods in the world. Relish in the array of locally owned shops such as gravitypope, FAWN, Kotn, and numerous vintage stores along the way. Grab a cup of coffee from White Squirrel Coffee Shop, named after the rare albino squirrels that inhabit Trinity-Bellwoods Park, located across the street.

Have lunch at modern French diner Le Swan or go for a light meal at Fresh (on Crawford Street), an outpost of a beloved local chain serving plant-based food since 1999. After lunch, take in the street art along Graffiti Alley, and then proceed south to snap a selfie on the Bathurst Bridge with the iconic CN Tower in the background. Check out stackt, a hip indoor/outdoor market of shops and services located in a complex made of shipping containers. In the evening, proceed to King Street West, where you will find some of the city’s most cherished dinner spots, like Buca, Lee, Le Select Bistro and Patria.

Day Two

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Start in Koreatown and grab a morning snack from Hodo Kwaja — this family run spot is known for their famous walnut cakes. Continue to The Annex, a lively area with many local businesses, cafes, and indie stores, like A Different Booklist – a unique spot specializing in multicultural books. You could even watch a film at Hot Docs Ted Rogers Cinema – a year-round venue screening documentaries (it's also home to North America's largest documentary film festival).

Arrive in the ritzy Yorkville neighborhood, where you'll find designer brands and several museums, including the Gardiner Museum, the Bata Shoe Museum, and the Royal Ontario Museum (ROM) – one of the largest museums in North America.

Next, head to Baldwin Village, where you can refuel in one of the quaint restaurants housed in old Victorian homes; we recommend stopping at Omai, a small Japanese fusion izakaya. You could also walk to nearby Chinatown for lunch — Asian Legend, Mother’s Dumplings, and Rol San are especially popular with locals. After lunch, continue your journey through Chinatown to Kensington Market – a multicultural, bohemian village, consisting of an array of specialty food vendors and shops. End your day with dinner and drinks at LOUIX LOUIS, located inside the St. Regis Hotel, and sip on one of the over 500 dark spirits available inside the restaurant’s two-story high Grand Bar. Save room for dessert and order the unforgettable, Instagrammable King’s Cake.

Day Three

If you visit during the summer, stroll along the city’s waterfront to take in the beautiful views of Lake Ontario. Start at the Toronto Music Garden, and then enjoy climbing up and down the award-winning Toronto Waterfront Wavedecks, whimsical wooden structures designed to mimic the shoreline of the province’s Great Lakes.

Walk to Toronto City Hall and snap a selfie with the iconic TORONTO Sign, or ice skate in the winter at Nathan Phillips Square. Learn about the city's history by visiting Old Town Toronto, the founding neighborhood of Toronto that has the largest concentration of 19th century buildings in the province, including Toronto’s First Post Office.

Break for lunch at St. Lawrence Market, a culinary destination home to 120 specialty vendors. Here, grab a classic Canadian peameal bacon sandwich from Carousel Bakery or a lobster roll from Buster’s Sea Cove. Spend the afternoon exploring the market and surrounding neighborhood. Take pictures of the iconic Gooderham Flatiron Building or the Berczy Park dog fountain, and grab an afternoon treat in quiet Corktown from one of Toronto’s best dessert shops, Roselle. Conclude your experience in Toronto by walking to the cobblestone Distillery District, a national historical site and arts hub. This unique location is home to art galleries, shops, and restaurants where you can toast to the end of your trip. Check out stunning El Catrin for Mexican dishes, or try Cluny Bistro, a modern French restaurant.

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