Toronto is one of my favorite cities in the world. Yeah, seriously—I love Toronto! I have visited Toronto twice, and on both trips I only spent about 48 hours in the city. Two days is enough to fall in love with this Canadian city!

Toronto is not necessarily a scenic city in the sense of traditional urban beauty nor is it a city designed for tourist attractions. What really stands out about Toronto is that it is a city that has a strong sense of place and a palpable soul—two qualities that would endear me to any city!

There are a few reasons I love Toronto so much are:

  1. Diversity: I love that you can walk around the city and see so many different types of people, restaurants, and cultures all existing together. Toronto is well known for this diversity and it feels very tangible when you are traveling there.
  2. Thriving Small Businesses: You can walk along one street, like Queen Street for example, and see shop after shop after shop, all seemingly doing quite well. There is such a creative and unique assortment of businesses, and I love that there is a minimal corporate presence in heart of Toronto.
  3. Delicious Food: No surprise as to why I love this, but Toronto has an awesome culinary scene. Although they aren’t Michelin accredited, they should be! There are definitely some James Beard and Michelin quality spots in the city, as well as amazing food trucks and hole in the wall spots.  

After raving about Toronto upon my return from my second visit to Canada’s largest city, I felt inspired to write a 2 day guide to exploring all the best that Toronto has to offer. I hope this inspires other folks to visit Toronto and spend 2 perfect days explore this amazing city. Wear comfortable shoes because you’ll be doing a lot of walking on this portion of your 48 hours in Toronto!

The Perfect 48 Hour Itinerary for Toronto, Ontario!

Toronto Skyline Canada

Day 1

Morning: St Lawrence Market & Distillery District

Start your first day in Toronto with some amazing food options in a historic building at St Lawrence Market. A perfect place to go with a small group of people with different tastes, this 208 year old market features over 100 different local food, drink, and handicraft producers. Lots of them offer samples and you can buy baked goods and snacks to fuel your walk! Please note that the market is closed on Mondays.

From the market, walk through Parliament Square Park until you hit your next stop—the Distillery District. This small neighborhood southeast of downtown Toronto is also a historic area of the city with roots going back to 1832 when the Gooderham and Worts Distillery was founded here. At the time, it was one of the largest distilleries in the world, and spanned across the 13 acre area. Today, you can still see the heritage buildings from the Victorian era with modern businesses and restaurants built inside the brick city.

In the Distillery District, you could easily spend a few hours eating and exploring! A few spots that I recommend checking out inside the district are Deciem, an abnormal beauty company that is all about self-love, City of Angels, a cute bohemian style women's clothing and gift store, and Biltmore, a cavernous vintage and new furniture shop with unique items to discover.

Afternoon: Walk the Neighborhoods

For me, the different neighborhoods are the best part of Toronto. Like the neighborhoods of Chicago that I love so much, Toronto is a city of neighborhoods and the “downtown” area is sterile compared to the vibrancy of the individual neighborhoods. Maybe I connect with this so much because it is similar to Chicago. The downtown is meh, while the neighborhoods really show the lifeblood of the city -- you can tell this is where Toronto locals actually spend their free time. 

Over the 5 days that I have spent in Toronto, I spent a majority of those just wandering around in the various neighborhoods of this city. There are several cool streets to enjoy that span several neighborhoods, but I might recommend starting with King Street West, Queen Street West, Dundas Street West or College Street West. All of these streets offer a thriving local boutique and restaurant scenes with stops every few storefronts to explore! I would usually have a few destinations in mind, like a shop or restaurant that I wanted to check out, which would guide my general direction but I left myself lots of time to discover things along the way.  

Shopping Boutique Toronto Ontario Canada

Evening: Food Adventures

Toronto is a city with a serious appetite. The food scene here is thriving and if they were Michelin approved, I guarantee there would be several Michelin star eateries. The diversity of food options here is astounding and I pinned far more restaurants on my custom Google Map than I could ever have gotten to in 48 hours in Toronto.

Regardless of which type of food you are in the mood for, Toronto has it. Because there are so many spots to explore, I recommend “bourdaining” which is my term for trying one dish at a lot different places in honor of Anthony Bourdain’s style of eating. This way, you can try a few restaurants around the city without filling up too much. Toronto is a large city, but I found that it isn’t serious about making advance reservations. There are places that take reservations in advance, but I found most of the time I just walked in and put my name on a list. As such, it is probably smart to dine in a smaller group of 4 or less people.

Day 2

Morning: Graffiti Alley and Downtown

Never one to turn down a good street art scene, I would recommend starting your second day in Toronto exploring the famed Graffiti Alley in the center of the city. Exactly as it sounds, this alley running behind Queen Street West is full of graffiti and street art. It offers a colorful explosion of creativity from local and international street artists. It changes every few months, so what you see on one visit might be completely different the next time!

From graffiti alley, you can continue walking east to downtown Toronto. If you get thirsty on the walk, stop in at Dineen Coffee Co or grab a bite to eat at the historic Queen Mother Cafe. In central Toronto, you can find the ‘grammable Toronto sign, city hall, Cloud Gardens, and Yonge-Dundas Square. If you have any hockey lovers in your travel group, the Hockey Hall of Fame is also located in downtown Toronto.

Graffiti Alley Toronto Ontario Canada

Afternoon: Kensington Market

Just north of Chinatown in central Toronto is Kensington Market. This walkable bohemian neighborhood feels like a hipster enclave in Toronto that attracts young artists and tourists to its indie shops, vintage boutiques, and arts spaces. Similar to the Distillery District, this historic small area has beautiful (and colorful!) Victorian homes that make it a great place to spend a few hours just wandering around.

It is no secret that I love shopping at independently owned boutiques, especially vintage clothing, so needless to say my favorite part of this neighborhood was all the vintage shops! Cinderella Vintage, Courage My Love and SubRosa were all great spots to dig for old treasures. There are plenty of other cool shops to explore in this area as well, like Cocktail Emporium where you can find all sorts of cool glassware, accessories and books for your next at-home cocktail party!

There are LOTS of food stalls, international restaurants and coffee shops to stop in as you walk around in Kensington Market. There are also some fine dining spots and wine bars if you’re feeling fancy! A few places of note are Blackbird Bakery for what might be Toronto’s best bread, Otto’s Doner for ‘grammable German street food, Wanda’s Pie in the Sky for a sweet or savory bite of pie and Grey Gardens for a stylish glass of wine.

Shopping Boutique Toronto Ontario Canada

Evening: Sunset Views & Cocktail Adventures

Before leaving Kensington Market, pick up some supplies to make yourself a little sunset picnic. As a waterfront city, Toronto has some beautiful skyline viewing spots and no time is better to enjoy Toronto’s cityscape than sunset. For the best views of the skyline, head to either Trillium Park or Jennifer Kateryna Koval's'kyj Park on the east or west sides of the city. Or if you’re more of a rooftop person, check out the stylish Rooftop Bar at the Broadview Hotel, SOCO’s Rooftop or the swanky Ritz Bar for amazing skyline views with tasty cocktails.

After the sun goes down, find a lovely spot to eat what is sure to be a great dinner.

Then, it is time to enjoy another awesome part of Toronto’s culinary scene—cocktails!Like many other cities around North America, Toronto is experiencing a resurgence of local distillers and mixologists coming together to revitalize the art of cocktail making. Civil Liberties, a bespoke cocktail bar is a great place to start. The bartenders will ask you about your liquor preferences and flavor profile, and then make a custom drink to suit your palate! The cozy and colorful Rhum Corner is another good spot, where you can try slushies or frozen tropical drinks. For something a little unique, head to the Lockhart, a Harry Potter themed bar that is cranking out some seriously good cocktails all inspired by characters or events from the books.  

Lockhart Harry Potter Bar Toronto Canada

Don’t forget any of these 2 day Toronto itinerary suggestions by pinning the image below!

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