A weekend in Toronto – summer edition (itinerary idea)

Toronto comes alive in the summertime —sunny patios spilling onto sidewalks, the skyline glittering across the lake, a food scene as diverse as its neighbourhoods, concerts and festivals filling every corner of the city with music and vibrant energy. If you’re planning a weekend in Canada’s largest city, here’s how to do it right: a mix of iconic sights, local gems, and a kayaking adventure that’ll have you seeing the city from a whole new angle.

Getting to Toronto

By Air: Fly into Toronto Pearson International Airport (YYZ), about 30 minutes from downtown (you can take an Uber or the UP Express right into the city), or Billy Bishop Toronto City Airport (YTZ), located right on the waterfront—perfect if you're coming from within Canada or nearby U.S. cities.

By Train: VIA Rail and GO Transit connect Toronto to major cities like Ottawa, Montreal, and Niagara Falls. Union Station is centrally located and close to many hotel options.

By Car: If you're driving, downtown Toronto is well-connected via major highways, but be prepared for traffic—especially during rush hour.

Where to stay

There’s no shortage of accommodation options for every type of traveller. Basing yourself downtown makes exploring easy! Here are a few recommendations to check out:

Budget-Friendly:

The Rex Hotel: A cozy, no-frills spot with live jazz and a Queen West address.

HI Toronto Hostel: Affordable, social, and walking distance to Union Station.

Mid-Range:

The Annex Hotel: Boutique, minimal, and surrounded by great coffee shops.

Ace Hotel Toronto: Stylish and centrally located with a rooftop bar.

Luxury:

1 Hotel Toronto: Sustainable luxury with lush greenery and chic design.

Bisha Hotel: Glamorous with rooftop views and a central Entertainment District location.

DAY 1 | Indulge in the food renowned scene

You’re in the big city! Once you’re checked in and freshened up, it’s time to dive into Toronto’s incredible food scene. The city is known for its incredible food scene (you can literally taste the world in one city) so of course the first thing you need to do is head out for a delicious dinner. Here are 5 of my favourite restaurants with a nightcap nearby:

Bar Isabel:

Spanish tapas in a cozy, dimly lit space that feels like a secret hideaway. Order the bone marrow and if you’re feeling adventurous, ask them for a luge.

Nightcap nearby: Bar Raval — a stunning Gaudí-inspired bar with craft cocktails and vermouth.

Mamakas Taverna:

Chic, modern Greek on Ossington with share plates and a lively atmosphere. Bar Koukla is nearby under the same owners and is a more casual version of this.

Nightcap nearby: Bellwoods Brewery — grab a seasonal craft beer on their patio.

Rasa:

Inventive, globally inspired dishes in a laid-back yet refined setting in the Annex.

Nightcap nearby: The Cloak Bar — an intimate speakeasy hidden below Marben Restaurant.

Sugo:

No-frills, old-school Italian known for their red sauce (and don’t miss the tiramisu, it’s the best in the city)

Nightcap nearby: Bar Neon — a cool, casual spot with a hidden back patio.

Oddseoul:

Korean fusion small plates on Ossington with hip, late-night energy.

Nightcap nearby: Cocktail Bar — a cozy, expertly crafted cocktail destination just down the street.

DAY 2 | Brunch + a slice of nature + a night out

Brunch is Toronto’s love language, so start your Saturday the way locals do—with a slow, satisfying meal in the west end.

For a standout brunch near Trinity Bellwoods Park, you’ve got two must-try spots:

· Saving Grace: A cozy, always-packed café with a rotating menu of globally inspired brunch plates (get there early—no reservations!).

· Lady Marmalade Café: Just steps from the park, this spot is a neighbourhood staple serving hearty eggs benedict and creative twists on classic brunch dishes.

After brunch, grab a coffee from Found Coffee, a local favourite tucked just off Queen West, and wander through Trinity Bellwoods Park—the city's social backyard. If it’s sunny, the park will be buzzing with picnics, dogs, and casual games of spikeball under the CN Tower’s distant gaze.

Next, make your way to the Jack Layton Ferry Terminal at the foot of Bay Street.

·       You can buy ferry tickets online or at the terminal kiosk—just $9.11 round-trip for adults.

·       Catch the Warden Island ferry, about a 15-minute ride across the harbour with skyline views that rival any postcard.

Once you arrive, walk a short distance to Toronto Island SUP & Kayak (follow the signs).

OT Pick Experience: Kayaking Through the Islands

Slip into your kayak and push off into the tranquil channels weaving through the island chain. These waterways are a pocket of calm just minutes from downtown, shaded by willows and lined with hidden lagoons. Paddle alongside serene houseboats, and feel the city’s pulse soften into nature’s rhythm.

Keep your eyes peeled for wildlife—turtles basking on rocks, swallows skimming the water, and maybe a heron or two standing silently in the reeds. The CN Tower pops up through the treetops, a gentle reminder of your proximity to the urban landscape.

The Toronto Island SUP team outfits you with a kayak, paddle, and route tips. Two hours out here is like stepping into your own personal escape—effortless, immersive, and restorative.

LOCAL TIP: Make sure you book your ferry and experience in advance as they both book up, especially in the summer months.

Book your kayaking experience on the Toronto Island SUP website.

Evening: King West Eats + Drinks

Once an industrial district, King West has transformed into Toronto’s go-to neighbourhood for a night out—lined with trendy restaurants, rooftop patios, and cocktail bars, all buzzing with energy once the sun sets.

• Gusto 101: Wood-fired Italian fare under a sprawling industrial ceiling and bright outdoor patio.

• Chubby’s Jamaican Kitchen: A cheerful spot with vibrant Jerk chicken and tropical cocktails.

• Anejo: A lively tequila bar and Mexican eatery with a massive tequila selection and a killer margarita menu. (I don’t like telling people this but it has the best happy hour in the city)

• Northern Maverick: A gorgeous patio, craft beers made in house and elevated pub fare

• Baro for Latin American share plates and a lively rooftop patio

Wherever you land, plan to linger—King West is the kind of place where one dinner often turns into drinks, music, and a second round somewhere nearby.

Local tip: make it a truly Toronto night by ending it with “street meat” aka a hot dog from one of the street vendors

DAY 3 | Skyscraper views, markets & neighbourhood wanders

Start your final day in Toronto with a morning at the iconic CN Tower—it’s touristy for a reason and doesn’t fail to impress. Tip: arrive early to beat the crowds. As you step into the high-speed elevator, it takes just 58 seconds to ascend over 1,100 feet, but it’s the moment the doors open that really stops you.

From the main observation level, the city sprawls endlessly in every direction—a living, breathing grid of glass, green spaces, and Lake Ontario glittering at the edge. Up here, you feel small in the best way, staring out at the sheer magnitude of Canada’s largest city, its urban pulse stretching far past what the eye can see.

Nowhere else in the world gives you this specific blend of towering skyline, islands floating in the harbour, and the vastness of a Great Lake on the horizon—it’s a perspective that’s uniquely Toronto.

If you’re feeling brave, step out onto the glass floor, where nothing but inches of glass separate you from the city streets far below. And for the ultimate view, go even higher to the SkyPod, one of the highest observation decks on Earth. From up here, on a clear day, you can see all the way to Niagara Falls and beyond—an experience that genuinely takes your breath away.

After soaking in the views, head 15 minutes east to St. Lawrence Market, where history meets food lover’s paradise. Skip breakfast elsewhere—this is where you’ll want to eat your way through the stalls.

Start with the iconic peameal bacon sandwich from Carousel Bakery—a Toronto classic. Then head downstairs to Uno Mustachio for one of their legendary Italian sandwiches, stacked high with veal parm, eggplant, or meatballs on a soft bun. St. Urbain Bagel serves up chewy, wood-fired Montreal-style bagels (go for an everything bagel with chive cream cheese). And for something sweet, stop by Blackbird Baking Co.—their butter tart is a must-try: flaky pastry filled with rich, gooey caramelized filling, just the right balance of sweet and indulgent, with that slightly sticky top that’s signature to a classic Canadian butter tart.

With your market cravings satisfied, take a 5-minute stroll south to Sugar Beach—a playful slice of waterfront where candy-pink umbrellas dot the white sand. It’s a peaceful, breezy spot to sit back, sip a coffee, and watch the ferries cruise toward the Islands while the skyline looms just behind you.

From Sugar Beach, head north on Jarvis Street for a few minutes, then cut west along The Esplanade until you reach Church Street. As you walk north, you’re not just following a route—you’re moving through layers of Toronto’s identity.

This stretch of Church Street takes you through The Village, Toronto’s LGBTQ2S+ hub and one of the most established gay villages in North America. It’s a neighbourhood known for its rainbow crosswalks, buzzing patios, and decades of activism that helped shape LGBTQ2S+ rights in Canada.

True to its name, Church Street is also lined with historic churches that tell the story of Toronto’s colonial and architectural past. St. James Cathedral, with its soaring spire, is the tallest church in Canada and a striking landmark in the downtown core. A few blocks further, you’ll pass St. Michael’s Cathedral Basilica, the seat of the Roman Catholic Archdiocese of Toronto, beautifully restored to highlight its Gothic Revival design and stained glass.

It’s a stroll that blends the sacred with the social—where grand stone churches share the street with queer bookstores, community spaces, and vibrant murals. In just a few blocks, you experience the full spectrum of what makes Toronto dynamic: its history, its people, and its pride.

Continuing your walk, head west toward Spadina Avenue, where you’ll land in the heart of Chinatown—one of the largest and most vibrant in North America.

The neighbourhood is a sensory overload in the best way: red and gold signage hanging from every storefront, the smell of freshly baked buns and roasted meats wafting from bakeries, and vendors spilling onto the sidewalks with baskets of exotic fruits like dragonfruit, lychee, and rambutan.

Take your time wandering the shops—some are packed with herbal medicines and teas, others with colourful ceramics and trinkets you didn’t know you needed. Stop by Ding Dong Pastries for a BBQ pork bun still warm from the oven, or grab a bubble tea from Kung Fu Tea to sip while you stroll.

Chinatown is layered with history too: while its current location flourished post-WWII, it’s a symbol of resilience, formed after the original Chinatown was displaced by urban development. Today, it stands as both a commercial hub and a cultural landmark that continues to evolve with new generations.

By the end of the day, you’ll have touched sky-high views, iconic city landmarks, markets, beaches, and neighbourhoods that each tell a different Toronto story—all within a weekend’s wander.

Ready to plan your trip to Toronto (and beyond)? Email travel@origin-travels.com for custom itinerary planning to get started with your adventure!