The Ultimate 4-Day Experience in Toronto, as Recommended by Locals

Toronto ranks as the fourth-largest city in North America, showcasing a dynamic skyline that continuously evolves. With its rich multicultural environment, it boasts an extensive network of parks and ravines, a stunning waterfront, towering skyscrapers, charming neighborhoods, and acclaimed restaurants, including Michelin and Hollywood favorites. (Having authored two cookbooks that highlight the city’s culinary gems, I can personally vouch for the incredible food scene.)

For an enjoyable long weekend escape, the best approach is to explore the city in segments, immersing yourself in its vibrant neighborhoods, parks, and attractions. Here’s a guide for four splendid days in Toronto.

Day 1: Explore the latest attractions and quirky parks in the Financial District

Typically, a city’s financial center isn't the first destination that comes to mind, but Toronto is breaking the mold. “It’s fascinating to witness the revitalization of the Financial District,” remarks Toronto Star social columnist, Shinan Govani. “Recently, many of the trendiest spots have sprung up here—pioneered by the new Milos.” Before its grand opening in late September, this Greek eatery hosted numerous exclusive parties during the Toronto International Film Festival, attracting celebrities like Francis Ford Coppola, Demi Moore, and Adam Driver. A workday meal of charcoal-grilled octopus and Canadian prime lamb loin with roasted potatoes is truly unbeatable.

Heading south, check out The Well, a vibrant new indoor-outdoor mixed-use development that serves as Toronto’s equivalent to The Grove in Los Angeles. Covering over seven acres in the King West district, it’s a hub for dining, shopping, working, and living. Govani highlights the modern restaurant Aera, located on the 38th floor of the 8 Spadina building, as a top spot for a meal: “Very sleek, offering a 360-degree view of the city, with a menu that resembles the finest room service options from a retro chic hotel.” (And that’s a good thing.) Sample new American favorites like chili chicken bites and the well-loved layered Filipino dessert halo-halo.

From here, it's a brief stroll to the Entertainment District at Front Street and Lower Simcoe. This vibrant area includes landmarks such as the CN Tower, Rogers Centre, St. Lawrence Market, Scotiabank Arena, and the Hockey Hall of Fame. Be sure to explore hidden treasures, like the three-tiered Berczy Park Dog Fountain, which features 27 dog breed sculptures—and one sneaky cat.

Day 2: Wander through Trinity-Bellwoods and Queen West

Kick off your morning with a coffee stroll at Trinity-Bellwoods, an urban park filled with lawns, playgrounds, tennis courts, and a designated off-leash area for dogs—Torontonians are big fans of their furry friends.

Just a block to the west lies the lively Ossington strip, stretching from Dundas Street to Queen Street, known as the city’s most exciting restaurant row. Pioneering spots like Foxley Bistro and Pho Rùa Vàng Golden Turtle Restaurant paved the way for places like Sweaty Betty’s bar and Bellwoods Brewery, followed by contemporary bistros such as Paris Paris, Côte de Boeuf, and Manita, renowned for having the best burger in town.

“There’s a lot of excitement surrounding the newly opened Linny’s,” notes Govani. “[Chef] David Schwartz has created a blend of classic steakhouse charm and 1980s deli vibes: a white-tablecloth establishment dedicated to his late mother.”

As you head east on Queen West, be sure to visit independent boutiques featuring locally crafted designer clothing, like Meg and Horses Atelier. Then, snap a photo in front of Graffiti Alley, situated just south of Queen Street West, between Spadina Avenue and Portland Street. When dinner rolls around, head to Waterworks, a newly opened European-style food hall housed in a heritage building, showcasing local indie culinary talents, including the stunning Civil Works on the second floor. This is the sister location to Civil Liberties, which made the World’s 50 Best Bars list in 2024.

The Greater Toronto Area runs along the northwestern shore of Lake Ontario and includes six local boroughs and cities. However, most visitors focus on downtown Toronto, which is easy to navigate, thanks to community advocates like Jane Jacobs, who played a key role in preventing the construction of downtown expressways, thereby preserving local neighborhoods just as Toronto was blossoming.

Day 3: Discover Kensington Market, Chinatown, and the AGO

“It’s undergone many changes, but I adore Kensington Market for its eclectic mix of restaurants and shops,” shares local TV and radio personality Pay Chen. This vibrant neighborhood, which emerged in the late 19th century to cater to Jewish and Italian immigrants, has retained its heritage while embracing new influences over the years. Indulge in smoked blue marlin and grilled shrimp tacos from Seven Lives, house-made charcuterie from local meats like Jambon de Paris at Sanagan’s Meat Locker, and sustainably sourced fish such as albacore tuna tataki at Hooked.

Adjacent to Kensington is one of North America’s largest Chinatowns, alive with bubble tea shops, eateries, shiatsu foot massage spots, and the renowned lacy pan-fried dumplings from the iconic (and Michelin-recommended) Mother’s Dumplings. At the far end of Chinatown stands the Frank Gehry-designed Art Gallery of Ontario (AGO), an architectural wonder showcasing a mix of ancient and contemporary artworks, alongside temporary exhibitions like “Bright Signs: Spotlight on Video Art” (running until October 14) and “Moments in Modernism,” which continues until September 1, 2025. Families will appreciate the interactive kids' center, and Grange Park lies just south of the AGO.

Day 4: Discover Toronto’s East Side

Toronto’s East Side, located east of the Don River, doesn’t attract as many visitors as other parts of the city due to its distance from downtown. However, it's definitely worth the ride on the 501 streetcar from the west side. The Beaches area, known for its expansive sandy shores along Lake Ontario, boasts family-friendly neighborhoods and charming Victorian-era streetscapes.

Before heading to the beach for a stroll along the boardwalk, be sure to stop by Maha’s Egyptian Brunch, where the honey cardamom latte exceeds expectations and pairs perfectly with fragrant fava bean foole and runny fried eggs served with charred baladi bread. After brunch, explore Little India on Gerrard Street and immerse yourself in the vibrant scents and sounds of this area stretching from Coxwell to Greenwood Avenue. Sample snacks at one of the many chaat houses or enjoy lunch at Lahore Tikka House, and shop at the Indian bazaar for everything from jewelry and spices to sweets and silks. If you visit during Diwali in November, you’ll be treated to a breathtaking sight as the bazaar sparkles with shimmering tea lights.

Where to Stay in Toronto

Four Seasons Hotel Toronto

Headquartered in Toronto, the Four Seasons hotel is located in the vibrant Yorkville neighborhood. It features the lively Café Boulud, a luxurious spa, and exceptional service that sets a global standard.

Ace Hotel

The first Ace hotel in Canada, designed by Shim-Sutcliffe Architects and Atelier Ace, boasts an irresistibly modern aesthetic—featuring sleek glass curves, lofty ceilings, and bold concrete. Inside, the inviting lobby lounge offers a warm welcome, but the real highlight is the 14th-floor cocktail bar, Evangeline, where the stunning city views come alive and the nightlife thrives.