The ultimate weekend in Toronto

Toronto’s skyline shimmers above the waters of Lake Ontario. The country’s largest metropolis is filled with attractions, from the Hockey Hall of Fame and St Lawrence Market to the diverse canvas of neighborhoods fanning out around the downtown core.

During my few heady years living there, do everything from chowing down late-night dumplings in Koreatown to sinking craft beer in Kensington Market, this energetic city felt like home away from home.

Here’s how to plan a perfect weekend in the city. 

• When to arrive: Arrive on Friday morning, drop your bags at your hotel and head out into the city. 

• How to get from the airport: Jump on the Union Pearson Express train from Pearson airport. It’s just a 25-minute ride to Union Station in Downtown Toronto and one-way costs $12.35 (US$9). Taxis and ride shares are more expensive and can take 30 minutes or longer, depending on traffic.  

• Getting around town: Toronto’s downtown is large but easy to navigate, and you can use local transit to reach certain places to save your legs a little. There are three TTC subway lines and Toronto’s abundance of bright red streetcars are ideal for traversing key east-west arteries like King, Queen and Dundas streets.

• Where to stay: Cosmopolitan Toronto can be pricey when it comes to accommodations, so book in advance if possible. For value, consider boutique stays a little out of downtown like local institution Drake Hotel and the Romanesque Revival-style Broadview Hotel in Toronto’s east end. Downtown, the proudly Canadian Four Seasons brand began in Toronto in 1961 and their flagship Four Seasons Toronto in Yorkville is the city’s finest luxury option. The art-focused BISHA offers a distinct collection of rooms, with pops of black and gold designed by rock star Lenny Kravitz’s own design studio.

• What to pack: Bring layers for winter months. Lake Ontario’s moderating presence means Toronto’s winters aren’t as cold as other Canadian cities, but you’ll still need a thick coat, scarf and hat. Meanwhile, breezy and light clothes are better in summer. At night, you can dress casually, but perhaps add a little more sparkle for downtown, especially in Yorkville. 

Day 1 

Morning 

Get to know downtown Toronto by taking a leisurely stroll among its streets and skyscrapers. Mos Mos Coffee has several spots between Yonge and University; grab caffeine and drop by Union Station for a closer look. Completed in 1927, its huge columns and grand Beaux-Arts architecture make the train station one of the city’s most prominent landmarks. Further along Front St, the quirky 19th-century Flatiron Building's narrow wedge shape is just as mesmerizing, especially with Toronto’s crystalline skyline behind. 

A large public market built in 1902, St Lawrence Market is a blur of color and aromas. Drop by Carousel Bakery for a taste of their famous and generously stuffed Peameal Bacon Sandwich (an Ontario specialty, peameal bacon is cured pork loin, rolled in yellow cornmeal). It’s filling, so you could treat this as breakfast or lunch.  

How to spend the day 

See the city from the CN Tower's 1150-ft-high observation deck. On a clear day, the distant Niagara Falls are visible across Lake Ontario, while its EdgeWalk - you’re strapped to a harness on the deck’s outer rim - is a nerve-shredding al-fresco option for those of a hardier disposition.

Back on (mercifully) solid ground, the red brick Steam Whistle Brewing roundhouse is one of Canada’s original independent breweries, and its airy industrial taproom is a unique spot for a cold beer and lunch at their kitchen. Stroll west up along Queen St West, where vintage boutiques and thrift stores sell everything from retro clothing to antique records. Check out the mural-splashed Graffiti Alley, and if the weather’s good, take a moment to relax in languid Trinity Bellwoods Park. 

Dinner 

Walk north through shaded residential streets to the lively Little Italy neighborhood on College St, where Danny’s Pizza Tavern offers red and white pies and massive signature martinis stuffed with olives. Across the street is Cafe Diplomatico, an Italian institution that’s been the heart of the neighborhood for generations.

For something a little different, drop by the delightful Singaporean kopitiam Kiss My Pans, where classics like Kaya toast and Beef Rendang are a flavor of chef and cofounder Jeanne Chai’s homeland. 

After dark 

Get craft beers at the historic Monarch Tavern or sip cocktails in the gorgeous Gaudí-esque, curved wood architecture of Bar Raval. Low-lit dive bar Ted’s Collision & Body Repair is a cool late-night hangout, while the century-old Mod Club hosts live gigs every weekend. 

Day 2

Morning

Head for Richmond St and find coffee at Fahrenheit Coffee before jumping on the 510 Spadina streetcar north through Chinatown and alighting at leafy Harbord St for breakfast at Emmer. The grassy-green Sicilian pistachio croissant is a favorite, and the covered patio is a breezy spot to enjoy sublime lunch sandwiches. Because this is a University of Toronto neighborhood, a number of inexpensive, student-friendly spots are around too, like toasted sandwich specialists TOROAST. 

How to spend the day 

Take a tranquil walk through university grounds, and make sure to glimpse the bizarre brutalist building that is the John P. Robarts Research Library on St George Street (some say it looks like a giant peacock, others think it’s a turkey or a dragon). Head up to the angular Royal Ontario Museum - a building of equally unique design - and explore its diverse collections running from dinosaur fossils and Egyptian mummies to exhibitions on costumes and textiles. For something a little more niche, see the Bata Shoe Museum's collection of 13,000 "pedi-artifacts," which includes pairs worn by Elton John and Queen Victoria.

Head back south to the Kensington Market, a bohemian neighborhood spilling with thrift stores, vintage shops and impromptu music performances, alongside taco joints and dive bars. Grab lunch at The Heartbreak Chef, where chef Jerome Robinson slings out mouthwatering fried chicken sandwiches and unctuous mac and cheese sides. Wash it down with a cold beer from one of my old haunts, Ronnie’s Local 069 (which is still as cash-only as it was when I once propped up the bar). 

Dinner 

Chinatown is where to find delicious dim sum (don’t miss Wok Theory’s delectable siu mai pork and shrimp dumplings), though if you want to go all out, consider making reservations at Canoe for some of the finest contemporary Canadian cuisine. Located high on the 54th floor of the TD Bank Tower, its glimmering views toward Lake Ontario are stunning at night; the menu focuses on slick Canadian-sourced dishes, like their Haida Gwaii albacore tuna in champagne and caviar sauce.

After dark 

Downtown Toronto is blessed with one of the country’s finest concert halls - especially for acoustics - so catch a show at the majestic neoclassical Massey Hall, built in 1894 just off Yonge St and attracting some of the world’s biggest artists. For live theater, the historic Ed Mirvish Theatre and the newer Princess of Wales Theatre both often draw the world’s hottest new productions.

Out in Toronto’s east end, the state-of-the-art music venue History is making waves for its curved interior, sloping floor and consistently good line-ups. 

Day 3 

Morning 

Spend the morning wandering among the red-brick Victorian factories and warehouses comprising the Distillery District, repurposed from the 19th-century Gooderham and Worts Distillery and lined with cafes, boutiques, restaurants and galleries. From downtown, it's a short stroll east on the 504 streetcar to the district’s photogenic cobbled streets. Pick up a pastry from Brick St Bakery or a coffee from Arvo.

How to spend the day 

Toronto is arguably the best place to understand Canada’s national sporting obsession, ice hockey.  Situated inside a handsome former bank, the Hockey Hall of Fame is a salute to the greats of the game, as well as an interactive walk through time. For tickets to Maple Leafs games, your best bet is resale sites like Ticketmaster and StubHub. It’s easier to get tickets for the Toronto Marlies, part of the American Hockey League, which feeds the NHL.

Make a serpentine stroll through bucolic High Park. Toronto’s largest public park, its undulating paths are wonderful for unwinding (though note that it becomes crowded during cherry blossom season), and its zoo boasts a curious collection of capybaras, llamas and even a yak.

Dinner 

Ease out of the park’s east entrance and head over to vibrant Roncesvalles, historically Toronto’s Polish neighborhood but now home to a variety of flavors. The silky pierogies and hearty soups at Cafe Polonez can’t be beaten. For something different, check out Chef Corinna Mozo’s easy-going Cuban joint La Cubana or affordable Japanese Musoshin Ramen.

After dark

Sip on smooth sake and Japanese whiskey at the low-key, 50s-inspired Black Dice Cafe before continuing on for a nightcap at Cocktail Bar (yes, that’s its name).