itinerary for Toronto Ontario

I’ve said it once and I’ll say it again, I love Canada! So when Paul invited me to tag along on a work trip to Toronto, I couldn’t say no.

Toronto is the provincial capital of Ontario, sitting along the shores of Lake Ontario. It’s the largest city in all of Canada, almost 3 million people call it home. This dynamic city is home to the Blue Jays (MLB) and one of the original six hockey teams, the Maple Leafs. A variety of local breweries, art museums and a castle (yes, a castle!) round out this Canadian destination.

As much as I love Canada, Toronto is my least favorite of Canada’s big cities. There’s no wow-factor. It seems to lack a bit of character. And although it sits on Lake Ontario, which is nice, there aren’t any mountains or jaw-dropping natural beauty, its quite flat. That being said, it’s still a nice city to explore and I would go back and give it another chance (Paul really wants to go to a Blue Jays game 😁).

itinerary for Toronto Ontario



The best time to visit Toronto is in the summer or fall. Summer temps hang in the mid-80’s with low humidity and refreshing lake breezes. In the fall, the changing leaves & start of the hockey season are reasons enough to visit!


Toronto is a big city with a laid back vibe, known only to Canada, but it’s also home to some great bars & restaurants. I tend to walk most of the time when I’m in a new city, so if you’re like me, be sure to bring comfortable walking shoes. In the summer, add a pair of sandals and in the fall/winter, a pair of waterproof Chelsea boots are perfect.  With the close proximity to the lake, it’s nice to have a light sweater or jacket even in the summer.


Staying downtown near the lake & financial district is a good spot. It keeps you centrally located and offers a lot to do in walking distance (or take advantage of their public transit).

itinerary for Toronto Ontario


  • Art Gallery of Ontario (AGO)
  • Explore Kensington Market Neighborhood
  • Graffiti Alley
  • Distillery District

Its kind of funny that I always start my vacation mornings with breakfast. When I’m at home all I have is coffee 😂. BUT, with that in mind, I do eat breakfast when I’m on holiday, because I love to eat and I enjoy finding unique spots. I stopped by Dineen Coffee Co. This charming coffeeshop is housed in a former fur clothing store (sad) and is one of the oldest building in Toronto. It’s listed as a Toronto Heritage Property and has a beautiful, colorful tiled floor and dark wood features.

itinerary for Toronto Ontario itinerary for Toronto Ontario

After filling up on coffee, I hit the streets of the Financial District. My first stop was the Bay Adelaide Center. Suits fans will recognize the exterior of this building, as it was the shooting location for Pearson Spector Litt. And although Suits isn’t my favorite show (anyone else think Harvey is kind of an arrogant ass?), as you might know, I do LOVE Meghan Markle, so I had to visit.


The Art Gallery of Ontario (AGO), has an exhibit I was really excited to visit. Yayoi Kusama’s Inifinity Mirrored Room, Let’s Survive Forever. This exhibit is ongoing (as of 2019) and is included in the price of admission. Let’s Survive Forever invites visitors to interact with a vision of infinity.

Let’s Survive forever is a small room filled with mirrors and glass balls, both suspended and placed across the ground – portraying an endless field of vision. Because this exhibit is best experienced alone (or with your small group), the museum allows everyone to have their own moment in the room. Each person (or group, up to 4 max) gets 60 seconds inside the room. I liked that I was able to go in by myself and have a quite moment alone.

itinerary for Toronto Ontario

The rest of the museum houses a lot of contemporary art. I studied art at university and the contemporary genre has never been my favorite. AGO does have a nice selection of European art from the 1300-1800s like Monet, Renoir, and other Italian works. Overall, if you like contemporary art, this museum is for you. If you don’t, I would recommend skipping AGO.


As I mentioned at the beginning of this post, I love to eat. And lunch and dinner fall perfectly into my wheelhouse. I headed to the Kensington Market neighborhood to have lunch at Seven Lives. Seven Lives is a small, cash-only taco spot.  I ordered one Cuitlacohce tacos (a vegetarian corn smut &  black bean taco). The tacos are pretty big but the space is pretty small. They only have one picnic style table that seats about six people. If you do want to try out their unique tacos, its good to note that there is usually a crazy line out the door. I got there about 15mins before opening and was the first in line – but by the time the doors opened, there were over 20 people behind me.


I spent the afternoon walking through Graffiti Alley. It’s a small area of graffiti-filled alleys, not far from Kensington Market. The whole space only takes up a few blocks. It’s a nice spot to walk around and window shop, as there are many shops along the streets.

itinerary for Toronto Ontario itinerary for Toronto Ontario itinerary for Toronto Ontario


itinerary for Toronto Ontario

That evening I met up with Paul and a few of his colleagues to explore the Distillery District. The Distillery District is a pedestrian-only entertainment district set in a 19th century whiskey distillery. It’s made up of multiple old brick buildings with cobblestoned streets. Inside the District you’ll find an array of local shops, hip bars and little art galleries.

itinerary for Toronto Ontario itinerary for Toronto Ontario

It’s a really fun area to explore. A couple of my favorite spots include Balzac’s Coffee Roasters and Mill Street Brew Beer Hall (the cherry cider rotation was delicious and they had a lot of vegetarian options). The area also has events going on throughout the year, including a traditional Christmas Market!

itinerary for Toronto Ontario itinerary for Toronto Ontario


  • Casa Loma
  • Hockey Hall of Fame
  • Bar Crawl

I started my morning at FIKA, a trendy little cafe housed inside of…. a house. The inside is light, bright and it has both a front and backyard patio for outdoor seating. I ordered their specialty drink – an iced coffee with oat milk, simple syrup, cardamom bitters & espresso. It was an unexpected flavor, I probably wouldn’t order it again. Also important to note, in the summer on the weekends, they don’t offer any WiFi.

itinerary for Toronto Ontario itinerary for Toronto Ontario itinerary for Toronto Ontario


When you think of Canada, do you think of castles? I know I don’t. But Toronto has one… and it’s gorgeous! Casa Loma is a Gothic Revival style castle built in the early 1900’s, known as Toronto’s Camelot. Sir Henry Pellatt designed the castle and filled it with expensive art, unique cars and secret passageways. Is a castle even a castle without secret passageways?

itinerary for Toronto Ontario

Today, it’s open to the public for tours. Casa Loma also hosts a variety of unique events including live Halloween theatre, escape rooms and concerts on the lawn. I highly recommend touring the castle and checking out an event!

itinerary for Toronto Ontario


While castles might not come to mind when you think Canada, Hockey definitely does! Toronto is home to the Hockey Hall of Fame (HHOF). The HHOF covers an expansive amount of the history of hockey. Thousands of Jerseys, equipment and memorabilia are on display. And so is the Stanley Cup! HHOF is home to the Cup, meaning, it lives here when it’s not out touring. I enjoy hockey and Paul LOVES hockey and we both thought the museum was really fun.

itinerary for Toronto Ontarioitinerary for Toronto Ontario


Ok who’s ready for a cold beer? Let’s head out for a Bar Crawl!

  • Steam Whistle Brewing | Built in old train yard, this brewery looks like its straight out of Thomas the Tank Engine (for my early-90’s friends 😂)
  • Amsterdam Brewery | Nice location on the water with lots of outdoor seating. Try their raspberry wheat beer, its light & refreshing
  • Rec Room | Next to Steam Whistle, arcade games + beer = a good time!
  • Bar Hop | Hipster bar with a lot of craft beer options


Below I’m listing some great bars & restaurants. Mix and match these into your day for lunch of dinner! They’re all unique with great cocktails, beautiful interiors and delicious food options.


While I’m a total sucker for a great view, I honestly was not impressed with the CN Tower. Although Toronto is on a Great Lake, as I mentioned above, the city is fairly flat and there isn’t much of interest to see from the top. It’s also quite pricey. Aside from the less-than-stellar views, it’s very loud & dirty at the top. I’d recommend going on a boat tour to get a look at the skyline instead of heading to the top of the CN Tower.

itinerary for Toronto Ontario

Why not PIN for later?

What’s your favorite Canadian city?

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