The Perfect 4-Day Toronto Itinerary

The Perfect 4-Day Toronto Itinerary
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It only took me 23 years to realize I was living a mere 10 hour drive from a country I had never been to. So a few weeks ago, my friend and I filled her car with snacks and booze and started the 600 mile drive to Toronto, Canada. Although it was far from a beach vacation, there’s still plenty to do in Canada during the wintertime. Read below for my ultimate 4-day Toronto itinerary and to see how I spent my first time in Canada.

Where to Stay in Toronto

The major perk of traveling to Canada in January is the ability to live out your wildest Airbnb fantasies. Since we were willing to drive north from a state that was already in the midst of a blizzard, we were able to rent the bougiest apartment in downtown Toronto for a fraction of the normal price! We rented this gorgeous place on the 22nd floor in the Entertainment District, complete with indoor parking and this spectacular view, for less than $80/night.

Find the listing here.

what to do in Toronto

My 4-Day Toronto Itinerary

Visit the St. Lawrence Market

As an avid traveler and a devoted foodie, there’s nothing I love more than a local market in a new city. St. Lawrence Market in Old Toronto is home to some of Toronto’s best eats, and you can’t beat the prices. Thankfully the market is indoors, so it’s the perfect place to spend an afternoon warming up and tasting some delicious Canadian cuisine!

Toronto vacation guide

Try Peameal Bacon Sandwiches from Carousel Bakery

No trip to the St. Lawrence Market is complete without sampling Carousel Bakery’s famous peameal bacon sandwich! Make sure to try it with their maple mustard for the perfect combination of savory and sweet.

Peameal bacon is a wet-cured, unsmoked bacon made from pork loin rolled in cornmeal. It’s found mainly in Southern Ontario, so make sure to try it when visiting Toronto.

Toronto Canada itinerary

And the Cheese Burek from Future Bakery

Still hungry? Head to Future Bakery to sample a range of international treats including sweet & savory burek and Pastéis de Nata, Portuguese custard treats.

Toronto vacation guide

Admire the Gooderham “Flat Iron” Building

Step outside the St. Lawrence Market for a fantastic view of the Gooderham, or the “Flat Iron” Building, and Toronto’s CN Tower. This famous building was designed in the 19th century for Toronto’s Gooderham family as the headquarters of their empire. Although many assume it was modeled after the Flat Iron Building in New York City, Toronto’s version actually predates the NYC landmark by a decade.

Toronto Canada itinerary

Take the Elevator 147 Floors Up the CN Tower

If you’re a fan of sensational views and spooky elevators, head to Toronto’s famous CN Tower and pay 38 CAD for a ticket to the top. If you’re feeling extra adventurous, and you’re visiting in the summer months, you can book tickets for the Edgewalk! For 200 CAD they’ll strap you in and scare you shitless as you walk around the very top of the tower…1,815 feet in the air.

Make sure to book your tickets to the CN Tower on one of your first days in Toronto. We waited until the last day and almost couldn’t get tickets due to a private event.

Toronto vacation guide

Nathan Phillips Square

Brave enough to experience a Toronto winter outside? Head to Nathan Phillips Square and ice skate your heart out in front of the city’s famous Toronto sign! No skates? No problem. Rent a pair on-site for only 10 CAD! Nathan Phillips Square was our first stop on our 4-day Toronto itinerary and, besides the bone-chilling cold, was the perfect introduction to Toronto.

things to do Toronto

Try Canadian Poutine

Fries? Good. Gravy? Good. Cheese curds? Good. All together = VERY good. This 4-Day Toronto itinerary is not complete without mention of Poutine. Poutine is a Canadian staple found on every street corner of Toronto. Although it’s all delicious, some places have a better reputation among locals than others. The best of the best is Poutini’s House of Poutine in Liberty Village. You can’t go wrong with the original, but if you’re feeling adventurous try one of their special creations like “The Works” with sour cream, bacon and chive.

Toronto vacation guide
Traditional: gravy, cheese curds and The Works: sour cream, bacon, chive.

Have Drinks at the Bier Markt

Could there be anything bad about a bar that serves over 150 beers on tap? Yeah I didn’t think so either. Bier Markt serves brews from all over the world, including a wide selection of local Canadian beers. My advice? Don’t limit yourself. Order a flight and taste four yummy beers at the same time!

Take a Half-Day Trip to Niagara Falls

With Niagara Falls only an hour and a half away, there’s no excuse to not take a half-day and experience one of the most famous national parks in North America. I’m not going to lie, there’s a lot more to do in Niagara Falls in the summer time. But do you know what there’s also a lot more of? People. If you’re interested in seeing spectacular views without the pesky crowds, head to Niagara in January and enjoy being one of the ten tourists brave enough to be outside during an Ontario winter.

If you do head down to Niagara Falls, I would suggest staying on the Canadian side. The views are much better!

things to do Toronto

Test Your Knowledge at the Royal Ontario Museum

There’s no better activity for a frigid Canadian day than exploring a museum! Well, besides maybe indoor drinking.

The Royal Ontario Museum is one of the largest museums in North America and the largest museum in Canada. It has every exhibit you could dream of: art, world culture, natural history and more. My personal favorite is the third floor, where they house the “Age of Mammals” exhibit as well as the “Age of Dinosaurs.”

Entrance tickets cost 23 CAD, but are only 18 CAD with a student ID.

4 day Toronto itinerary

Explore Toronto’s Historic Distillery District

The Distillery District of Toronto is filled with hip and trendy boutiques and restaurants housed in 19th century whiskey distillery buildings. It’s the perfect neighborhood to do some shopping or enjoy a happy hour. During Christmastime, the streets are filled with Toronto’s Christmas Markets.

4 day Toronto itinerary

Sample Local Cheese and Sauces at Wildly Delicious

While you’re wandering the quaint, cobblestone streets, stop by Wildly Delicious for a taste of Toronto’s finest. They sell plenty of sweet, Canadian maple syrup as well as home goods and every kind of sauce, chutney and cheese you could imagine!

Wander Through Graffiti Alley

Although I’ll admit it’s not the best activity for a freezing day in Canada, Graffiti Alley is definitely worth a quick visit. Wander the narrow alleyway, admire the colorful street art…and maybe warm up with a hot chocolate afterwards.

4 day Toronto itinerary

Where to Eat in Toronto

Now for the highlight of my Toronto vacation guide! Like every major city, Toronto has no shortage of yummy eats. Make sure to eat your fill at these delicious restaurants before you head home!


Featured by INSIDER Food, Menami serves Udon noodles with a delicious twist. Thick and doughy noodles are topped with creamy cheese sauce and shredded tex-mex cheese before being baked to perfection. It’s the perfect mix of traditional udon and mac n’ cheese!

4 day Toronto itinerary
Fresh fried ika, mentaiko cream sauce udon, oven baked udon.

Chinatown’s The Dumpling House

To say we left full would be a gross understatement…a dumpling coma might be more accurate. The Dumpling House sells traditional dumplings both steamed and fried with a variety of fillings. It was also one of the most affordable restaurants we ate at in Toronto. If you do decide to try it out, learn from our mistake and don’t order any appetizers. We were uncomfortably full until the next day, but nothing warms you up like fresh dumplings!

4 day Toronto itinerary
Steamed seafood dumplings, pork & shrimp pan-fried dumplings, egg drop soup.

Pancho’s Bakery

Soft serve in a churro cone? Enough said. Right around the corner from The Dumpling House, Panchos’ Bakery serves this Instagrammable mash-up treat. Although probably enjoyed best in the summer, the juxtaposition of the freezing ice cream and the warm churro made the treat even more enjoyable.

4 day Toronto itinerary
Churro ice cream cones.

Chubby’s Jamaican Kitchen

Not only does Chubby’s serve up delicious and authentic Jamaican cuisine, but their restaurant is an Instagram dream. The inside is covered in pink lights and plants and the whole restaurant smells like smoky pork and fried plantains. They also offer a full menu of fancy cocktails topped with edible flowers and whipped egg whites!

4 day Toronto itinerary
Jerk pork, fried plantains, jasmine rice.


Sometimes while traveling, a girl just needs a full brunch and a spicy bloody mary. Eggspectation is the perfect combination of American brunch with a Canadian twist. Now I’m convinced that the only thing that makes poutine better is a fried egg on top!

what to eat in Toronto
Bloody Mary, bagel & lox, breakfast poutini.

Little Italy’s Pizzeria via Mercanti

What better place for a girl missing Italy than a pizzeria in Little Italy? Pizzeria via Mercanti was a little slice of heaven with tasty vino, fluffy Neapolitan pizza and an Italian-speaking waitstaff. We enjoyed some authentic Neapolitan pizza and ended the meal the right way, with an espresso and an ice-cold limoncello.

Toronto vacation guide
Margherita pizza, via Mercanti pizza, house red wine.

Even in the frigid Canadian winter, there’s plenty to see, do and eat in Toronto! I recommend staying for at least a long weekend to truly enjoy your time there.

Thanks for reading and if you enjoyed this 4-day Toronto itinerary don’t forget to subscribe to my blog and follow my adventures on Instagram @madisonfootsteps! You also might enjoy my posts


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  1. Monika
    February 15, 2020 / 1:52 PM

    Looks like a great place to visit with plenty to do and eat! Chubby’s kitchen sounds so good! Plantains= yum! I also love that you went to Niagara Falls in January. I love following your adventures 🙂

    • March 1, 2020 / 5:27 PM

      It was delicious, if you’re ever in Toronto you have to go 🙂 It was worth it but also ridiculously cold haha!

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