Toronto is huge. Like, confusingly huge. If you try to see everything in a weekend, you'll just end up spending four hours staring at the brake lights of a Lexus on the Gardiner Expressway. It's a mistake people make constantly. They think they can hit the CN Tower, the ROM, a game at the Rogers Centre, and dinner in Yorkville all in one go. You can't. Not if you actually want to enjoy yourself, anyway.
Spending 36 hours in Toronto requires a strategy. You have to pick a vibe and commit to it. Most people think Toronto is just a smaller, cleaner New York, but that’s a lazy comparison. It's more like a collection of distinct villages that accidentally grew into a massive metropolis. Honestly, the best parts of the city aren't the big glass towers; they’re the narrow alleyways in Kensington Market and the weirdly quiet residential streets of Cabbagetown.
If you're landing at Pearson (YYZ), take the UP Express. Don't even look at the taxi line. It's twenty-five minutes to Union Station, and it saves you from the literal hell of Friday afternoon traffic. Once you're downtown, drop your bags and get moving. You’ve only got a day and a half.
Friday Night: The West End Shuffle
Start in West Queen West. Vogue called it one of the coolest neighborhoods in the world a few years back, and while the rent has skyrocketed since then, the energy is still there. Walk past Trinity Bellwoods Park. If it’s even remotely warm outside, half the city will be sitting on the grass with "disguised" cans of local craft beer from Bellwoods Brewery. It’s a scene.
For dinner, skip the stuffy hotel restaurants. Head to Imanishi Japanese Kitchen on Dundas West. It’s located in what looks like an old auto body shop or a dive bar, and they don't take reservations, so you might have to wait. Get the corn kakiage and the tebasaki wings. It’s chaotic and loud and exactly what the city feels like right now.
Why the CN Tower is a "Maybe"
Look, the CN Tower is impressive. It was the world's tallest freestanding structure for decades. But standing in line for two hours to pay $45 for a view you can get for the price of a cocktail elsewhere? Kinda questionable. If you really want the skyline shot, go to the Writer's Room Bar at the Park Hyatt in Yorkville or the Broadview Hotel’s rooftop in the east end. You get the tower in your photos, which is much better than being inside it.
After dinner, if you aren't exhausted, grab a drink at The Horseshoe Tavern. It’s a legendary spot. Everyone from the Rolling Stones to Arcade Fire has played there. It smells like old beer and history. It’s perfect.
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Saturday Morning: Markets and Messy Breakfasts
Wake up early. You need to get to Kensington Market before the crowds get unbearable, though "early" in Kensington usually means 10:00 AM because nothing opens before then. It’s a designated National Historic Site and for good reason. It’s one of the few places left that hasn't been scrubbed clean by developers.
- Fika Cafe: Grab a coffee and sit in their back patio.
- Seven Lives Tacos: The Gobernador taco is famous for a reason. It’s messy. It’s salty. It’s incredible.
- Nu Bügel: Best bagels in the city, fired in a wood-burning oven. Sorry, Montreal, these are actually competitive.
Walk from Kensington over to the Art Gallery of Ontario (AGO). Even if you aren't an "art person," the building itself is a masterpiece. Frank Gehry, who grew up in the neighborhood, designed the massive wood-and-glass staircase that looks like a ship's hull. Check out the Indigenous art collection on the first floor. It’s world-class and offers a perspective on Canadian history that you won't get from a gift shop postcard.
The Distillery District Trap
By Saturday afternoon, you’ll probably be tempted to head to the Distillery District. It’s beautiful—cobblestone streets, Victorian industrial architecture, very "Instagrammable." But it’s also a bit of a tourist bubble. Go there for the Soma Chocolatemaker (the micro-batch chocolate is legitimately some of the best in North America) and maybe a quick photo, but don't spend your whole afternoon there.
Instead, hop on the 504 King streetcar heading east. Get off at River Street and walk into Corktown Common. It’s a park built on an old industrial site that doubles as a flood plain. From there, you can walk across the bridge into Riverside and Leslieville.
Eating your way through the East End
The East End is where the "real" Toronto lives. It’s quieter, leafier, and has better food.
- White Lily Diner: Old-school vibes with high-end sourcing. Their smoked fish platter is a revelation.
- Ed’s Real Scoop: Get the burnt marshmallow ice cream. Just do it.
- Tabule: If you want Middle Eastern food that blows your mind.
Toronto’s diversity isn't just a marketing slogan; it's the city's actual DNA. Over 50% of the population was born outside of Canada. This means you can get authentic Tibetan momos in Parkdale, incredible Greek food on the Danforth, and some of the best Dim Sum in the world in Spadina’s Chinatown, all within a twenty-minute transit ride. Your 36 hours in Toronto should reflect that. If you only eat burgers and pasta, you're doing it wrong.
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Saturday Night: Choosing your own adventure
If you're into sports, and the Leafs or Raptors are playing, the area around Scotiabank Arena will be electric. But tickets are expensive. Like, "sell a kidney" expensive. A better bet is catching a Toronto FC match at BMO Field if it’s soccer season. The atmosphere in the south stand is wild.
For a nightcap, head to The Gift Shop. No, it’s not a place to buy magnets. It’s a speakeasy hidden in the back of a barber shop on Ossington. The drinks are stiff, the lighting is low, and nobody will find you there.
Sunday: The Island Escape
Before you head back to the airport or the train station, you have to do the Islands. This is non-negotiable. Take the ferry from the Jack Layton Ferry Terminal.
Pro Tip: Don't take the Ward's Island ferry if you want the beach; take the one to Hanlan’s Point or Centre Island. But actually, Ward's is better for walking because it's a residential community with no cars and tiny, beautiful cottages that look like they belong in a storybook.
Standing on the edge of the island looking back at the skyline is the only way to truly grasp the scale of the city. You see the wall of condos, the CN Tower sticking up like a needle, and the massive cranes that indicate Toronto is still growing at a frantic pace. It's a quiet moment before the rush of leaving.
Practical Logistics for your 36 hours in Toronto
Don't bother renting a car. You will regret it the moment you hit the 401. Toronto's transit system (the TTC) is decent, though we locals love to complain about it. You can pay by tapping your credit card or phone on any bus, streetcar, or subway gate.
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Where to stay:
- The Drake Hotel: Not the rapper. The hotel. It’s the cultural hub of Queen West.
- 1 Hotel Toronto: If you have the budget and want that "eco-luxury" feel.
- The Broadview Hotel: Great if you want to explore the east side.
Weather Reality: If you come in January, it’s freezing. If you come in July, it’s humid enough to feel like you’re breathing through a wet towel. May, June, September, and October are the "Goldilocks" months.
Toronto isn't a city that reveals its charms immediately. It’s not Paris; it’s not flashy in that way. It’s a city of layers. You have to peel them back. You have to walk until your feet ache and eat things you can't pronounce.
Next Steps for your trip:
- Download the Green P app: If you ignored my advice and rented a car, this is the only way to pay for parking without losing your mind.
- Book your dinner reservations: Use OpenTable or Resy at least two weeks out for popular spots like Bernhardt’s or Dreyfus.
- Check the festival calendar: Between TIFF in September, Luminato in June, and Nuit Blanche in the fall, there is almost always a massive street festival closing down a major road. Plan your transit accordingly.
Go walk the subterranean PATH tunnels if it rains—it’s 30 kilometers of underground shopping that connects the entire financial district. It's weirdly dystopian and fascinating at the same time. Just don't get lost; even the people who work there don't really know where all the exits go. Enjoy the 6ix. It’s a lot better than the locals will lead you to believe.