Toronto is a city that effortlessly blends history, culture, and modern luxury. Whether you’re a local looking to explore your city or a visitor wanting to experience the best it has to offer, there’s no better place to spend a weekend than downtown Toronto. It’s no wonder many Toronto realtors often highlight the city’s dynamic lifestyle when showcasing homes in the area—there’s always something new to discover.
From its vibrant food scene to its rich historical landmarks, this two-day itinerary offers the perfect balance of relaxation, exploration, and indulgence—all while steering clear of the more “guidebooky” locales. Let’s dive into your unforgettable weekend in downtown Toronto.
Saturday: Explore the Heart of the City
Morning: Brunch at Saving Grace
Begin your day at Saving Grace, a cozy café nestled at 907 Dundas Street West. This charming spot, often compared to a friend’s stylish apartment, is known for its intimate atmosphere and inventive, ever-changing brunch menu. Signature dishes like Eggs Rajasthani, featuring spicy scrambled eggs, and Caramelized Banana French Toast keep locals and visitors coming back for more. Due to its popularity, especially on weekends, expect a wait—though the unique flavors and cozy vibes make it well worth the patience.
Midday: Stroll Through Kensington Market
After brunch, head to one of Toronto’s most eclectic neighborhoods—Kensington Market. This historic area is a microcosm of Toronto’s multicultural identity, brimming with vibrant street art, unique vintage shops, and a mix of international food options. As you wander through its narrow streets, take the time to explore some of the independent boutiques selling everything from hand-crafted jewelry to locally roasted coffee beans.
For foodies, this is a must-visit spot. Grab a fresh empanada, savor some churros, or enjoy a refreshing bubble tea as you explore. Kensington Market is also home to some of the city’s best street art, with murals that change frequently, adding to the ever-evolving character of the neighborhood.
Afternoon: Artistic Immersion at MOCA and Graffiti Alley
For a more unique art experience, skip the Art Gallery of Ontario (AGO) and head to Toronto’s Museum of Contemporary Art (MOCA) instead. Located in the Junction Triangle, this vibrant space showcases rotating exhibits of contemporary artists who push the boundaries of art and culture. From interactive installations to thought-provoking photography, MOCA is a haven for modern art enthusiasts. The museum’s industrial-chic vibe, housed in a converted aluminum factory, makes the visit even more memorable.
After MOCA, take a short drive to Graffiti Alley, Toronto’s open-air gallery for street art. This colorful stretch of alleyway off Queen Street West is a hidden gem, with constantly changing murals from local and international artists. It’s a perfect spot for both art lovers and Instagrammers alike. Cap your artistic tour off with a visit to The Annex, which plays host to several galleries, live music venues, literary cafes, and cultural landmarks.
Evening: Dine at a Landmark Restaurant
After a day of exploring, treat yourself to an upscale dining experience. Canoe, located on the 54th floor of the TD Bank Tower, offers breathtaking views of the Toronto skyline alongside a menu that celebrates the best of Canadian cuisine. Whether you’re indulging in their locally sourced meats or enjoying fresh seafood, this is the perfect spot to cap off your day with a luxurious meal.
Alternatively, head to Scaramouche, a Toronto institution known for its elegant atmosphere and French-inspired menu. Their famous coconut cream pie is the perfect ending to a decadent dinner. Reservations are recommended for both spots to ensure you get the full experience.
Sunday: Leisure and Luxury
Morning: Relax in Yorkville
Start your Sunday with a relaxing breakfast in Yorkville, Toronto’s luxury shopping district. A favorite among locals is Hemingway’s, a casual yet charming spot that serves up classic breakfast dishes like eggs and toast, pancakes, and fresh fruit bowls. If you’re in the mood for something more refined, try Sassafraz, a Yorkville institution known for its beautiful patio and upscale breakfast options like truffle scrambled eggs or their famous brunch burger.
After breakfast, it’s time for some retail therapy. Take a stroll through Yorkville’s boutique-lined streets, where you’ll find everything from high-end designer stores like Gucci and Louis Vuitton to charming independent art galleries. Whether you’re picking up the latest fashion trends or indulging in luxury shopping, Yorkville is the place to treat yourself. Make sure to take a walk through the Royal Ontario Museum (ROM), which is just a short distance away. With its vast collection of artifacts and natural history exhibits, the ROM is a treasure trove of arts and culture. Whether you’re admiring ancient sculptures or marveling at contemporary exhibits, this museum offers something for every kind of art lover.
Midday: Hidden Gems in The Junction and Wychwood Barns
Instead of the more touristy waterfront or Distillery District, why not explore two of Toronto’s most underrated neighborhoods? Start your afternoon in The Junction, a neighborhood known for its eclectic charm and prohibition-era history (it was a dry community until 1997). The Junction is full of quirky boutiques, antique shops, and small art galleries. Make a stop at Latitude 44 Gallery Framing for unique, locally produced art and handcrafted pieces that you won’t find anywhere else. While you’re here, grab a coffee at The Good Neighbour or indulge in locally sourced bites at Nodo, a cozy Italian eatery.
Next, head over to Wychwood Barns, a community hub and cultural space that flies under the radar. Once home to Toronto’s streetcars, it’s now an arts and environmental center with a weekly farmers’ market, local art exhibits, and a sustainable garden. If you’re lucky, you might catch a live performance or community art show. This peaceful escape feels worlds away from the busy city streets and is perfect for a midday stroll.
Afternoon: A Spa Break at the Shangri-La
For the ultimate in relaxation, book a spa treatment at the Shangri-La Hotel’s Miraj Hammam Spa. This Middle Eastern-inspired spa offers a range of luxurious treatments, from traditional hammam experiences to deep-tissue massages and revitalizing facials. After a weekend of exploring the city, there’s no better way to unwind than with a soothing spa session in one of the city’s most opulent settings.
If you’re looking for something a bit more local, Body Blitz Spa is a women-only spa known for its unique water circuit, which includes a warm Dead Sea salt pool, a cold plunge pool, and an herbal steam room. It’s a tranquil oasis in the heart of the city, perfect for a quiet afternoon of self-care.
Evening: Sunset Drinks with a View
Finish off your weekend with sunset drinks at Lavelle, a rooftop bar and restaurant offering 360-degree views of the city. Located on King Street West, Lavelle’s chic poolside atmosphere and creative cocktail menu make it the perfect spot to reflect on your weekend in Toronto. Order a refreshing Aperol Spritz or a signature cocktail, and enjoy the stunning views of the CN Tower as the sun sets over the city.
For those looking for something a bit more low-key, consider The Drake Hotel Sky Yard, another rooftop gem located in the heart of Queen Street West. With its laid-back vibe, friendly service, and seasonal drink menu, it’s a great way to close out a weekend filled with both adventure and relaxation.
Downtown Toronto offers a vibrant mix of activities, whether you’re looking to explore its cultural landmarks, enjoy its top-tier restaurants, or simply relax in one of its luxurious spas.
This off-the-beaten-path weekend itinerary gives you a taste of everything Toronto has to offer. And with so many options for getting around the city, you can easily explore these iconic neighborhoods without missing a beat. Whether you’re visiting for the first time or rediscovering your own city, this weekend promises to leave you with unforgettable memories of downtown Toronto.
