Toronto is the fourth-largest city in North America, with an ever-changing skyline. It has a multicultural urban landscape with a park and ravine network that stretches from end to end, plus a waterfront, skyscrapers, genteel neighborhoods, and Michelin and Hollywood stars. (As someone who has written two cookbooks featuring the city’s best restaurants, I can personally attest to the deliciousness of the food.)
For a long weekend getaway, it’s best to attack the city in sections, winding your way through diverse neighborhoods, parks, and attractions. Here’s how to spend four delightful days in Toronto.
Day 1: Hit up the Financial District’s latest stars and whimsical parks
While a city’s business hub is usually the last place you’d think of visiting, Toronto is bucking the trend. “It’s interesting to see new signs of life in the Financial District,” says Toronto Star’s social columnist, Shinan Govani. “A lot of the hottest spots have emerged here recently—led by the new Milos.” Before it officially opened in late September, the Greek restaurant hosted a slew of secret Toronto International Film Festival parties with guest lists that included Francis Ford Coppola, Demi Moore, and Adam Driver. A workday lunch of charcoal-broiled octopus and Canadian prime lamb loin with roasted potatoes can’t be beat.
Heading south, visit The Well, a new indoor-outdoor mixed development that’s like Toronto’s answer to The Grove in Los Angeles. Spanning more than seven acres in the King West area, it’s an eat, shop, work, and living hub. Govani says contemporary restaurant Aera, on the 38th floor of the 8 Spadina building, is a favorite for grabbing a meal: “Very slick, with a 360-view of the city, and a spread that reads like the best room-service menu in a retro haute hotel.” (A good thing.) Try new American classics like chili chicken bites and the popular layered Filipino dessert halo-halo.
From here, it’s a short walk to the Entertainment District at Front Street and Lower Simcoe. The area encompasses the CN Tower, Rogers Centre, the St. Lawrence Market, Scotiabank Arena, and the Hockey Hall of Fame. But don’t miss less obvious gems, like the three-tiered Berczy Park Dog Fountain, which features 27 sculptures of dog breeds—and one hidden cat.
Day 2: Stroll the Trinity-Bellwoods and Queen West
Start the morning off with a coffee stroll at Trinity-Bellwoods, which is an urban park full of lawns, play structures, tennis courts, and an off-leash dog area—Torontonians love their dogs.
Just a block west is the hot Ossington strip, which runs from Dundas Street to Queen Street and is the city’s most dynamic restaurant row. Early adopters Foxley Bistro and Pho Rùa Vàng Golden Turtle Restaurant got the ball rolling, which begat Sweaty Betty’s bar and Bellwoods Brewery, followed by modern-era bistros like Paris Paris, Côte de Boeuf, and Manita (home to the best burger in town).
“There’s also a lot of buzz about the just-opened Linny’s,” says Govani. “[Chef] David Schwartz has gone the route of an old-school steakhouse–meets–1980s deli: a white-tablecloth spot that is a tribute to his late mother.”
Heading east on Queen West, pop into some of the independent shops featuring locally made designer clothing, such as Meg and Horses Atelier, then strike a pose in front of Graffiti Alley, located just south of Queen Street West, between Spadina Avenue and Portland Street. Finally, it’s time for dinner and cocktails at Waterworks, a just-opened European-style food hall in a heritage building full of local indie food and beverage stars, such as the gorgeous Civil Liberties on the second floor. It’s the sister location to the original in Bloorcourt Village, which landed on the World’s 50 Best Bars list in 2024.
The Greater Toronto Area stretches along the northwestern shore of Lake Ontario and comprises six local boroughs and cities. But the focus for most visitors is downtown Toronto, accessible and easy to explore thanks to community-based city-planning champions like Jane Jacobs, who helped stop downtown expressways from being built, protecting local neighborhoods just as Toronto was coming of age.
Day 3: Explore Kensington Market, Chinatown, and the AGO
“It’s changed a lot, but I love Kensington Market for its restaurants and shops,” says local TV and radio host Pay Chen. A busy neighborhood, born in the late 19th century to serve local Jewish and Italian immigrants, Kensington Market has kept the old while welcoming the new over the decades: Think smoked blue marlin and grilled shrimp tacos from Seven Lives, house-made charcuterie from locally sourced meats, like Jambon de Paris at Sanagan’s Meat Locker, and sustainably caught fish like albacore tuna tataki at Hooked.
Abutting Kensington is one of North America’s largest Chinatowns, bustling with bubble tea shops, restaurants, shiatsu foot massages, and the best lacy pan-fried dumplings at city institution (and Michelin recommended) Mother’s Dumplings. At the tail end of Chinatown is the Frank Gehry–designed Art Gallery of Ontario (AGO), an architectural marvel filled with ancient and modern works, plus traveling exhibitions like “Bright Signs: Spotlight on Video Art” (on until October 14), and “Moments in Modernism,” ongoing until September 1, 2025. There’s also a hands-on center for kids, and the Grange Park is just south of the AGO.
Day 4: Explore Toronto’s East Side
Toronto’s East Side, which refers to the area east of the Don River, doesn’t get a lot of visitors compared to other areas of Toronto, as it’s removed from the downtown core. But it’s well worth the straight shot on the 501 streetcar from the west side. The Beaches area, named for its vast stretches of sandy beaches on Lake Ontario, is full of family-minded neighborhoods and Victorian-era streetscapes.
Before hitting the beach for a boardwalk stroll, join the line at Maha’s Egyptian Brunch, where the honey cardamom latte is even better than it sounds, perfect with fragrant fava bean foole and runny fried eggs with charred baladi bread. After brunch, visit Gerrard Street’s Little India and be utterly transported by the scents and sounds of this enclave that runs from Coxwell to Greenwood Avenue. Grab a snack at one of its many chaat houses—or lunch at Lahore Tikka House—and shop at the Indian bazaar for everything from jewelry and spices to sweets and silks. Visiting during Diwali in November is especially gorgeous, as the bazaar is filled with shimmering tea lights.
Where to Stay in Toronto
Four Seasons Hotel Toronto
- Book now: fourseasons.com/toronto
With the mother brand headquartered in Toronto, the Four Seasons hotel sits in the heart of the Yorkville neighborhood. It has the lively Café Boulud, a stunning spa, and impeccable service that sets the global tone.
Ace Hotel
- Book now: acehotel.com/toronto
The first Ace in Canada, this hotel was designed by Shim-Sutcliffe Architects and Atelier Ace and is as sexy as a building gets—all glassy curves, soaring ceilings, and steely concrete. Inside, the cozy lobby lounge is welcoming, but the 14th-floor cocktail bar Evangeline is where the cityscape shines and the partying happens.
