Postcards & Passports

Discovering Toronto with Urban Expeditions

This post was most recently updated on July 9th, 2019

How would you go about discovering Toronto on a first-time visit? Would you check the top ten list of things to do on TripAdvisor? Or the tourist pamphlets in your hotel’s reception area? There’s actually another way to familiarize yourself with a new city — taking an urban tour. One of the newest concepts in travel today is “Urban Tourism”.

Urban tourism…what exactly does that mean? It’s getting to know the city where you are…the history, the culture, the people, and the space. Whether it’s where you live…or a city you are visiting, urban tourism is all about making real connections. On a recent visit to Toronto, my husband and I got to experience urban tourism firsthand with Peter Odle and Urban Expeditions.

Discovering Toronto

I had no idea what to expect. We were told to pack light and bring an extra pair of socks. Peter met us in our hotel lobby and hailed us a cab to meet up with another ‘urban tourist’ (Robina, from Holland) who would be joining us in discovering Toronto.

This tour would be unlike any I’ve ever experienced. First of all, Peter was incredibly knowledgeable about Toronto, and its history. It was also clear that he truly loved the city of Toronto. It’s where he lives and works and it’s where he vacations. In fact, I’d say he was refreshingly passionate about us discovering Toronto for ourselves! We figured since Toronto is the largest city in Canada, it was a good place to start.

The Tour begins

We started our tour in west Toronto, near where the original fort was established by the British in 1793. As we walked (pretty quickly, I might add!), he told us about the origins of Toronto: how it got its name, who settled it, who fought for it, and how it began to grow and expand. He shared with us the struggles of the immigrants who came, disasters (like major fires) that defined the people and the city, and the politics of overcoming differences between nationalities, religious beliefs, industries, and more.

We walked through neighborhoods of early row homes, originally built in wood, but re-built in brick after the 1904 fire. We learned how early Toronto residents adapted — to the cold, to poverty, and to the need to expand industry and education. Peter shared the three main keys to Toronto’s growth: bricks, booze, and pigs (or bacon, if you want to keep it all B’s!).

We learned about failed housing projects, revitalization efforts, and transportation issues. (Should the underground metro be expanded? What about the sleek electric trolley system that gets shut down by automobile accidents because they share the same roads?)

Hidden Gems

Peter led us around the University of Toronto and its colleges, buildings inspired by English architecture, and beautiful hidden courtyards, study nooks, and park spaces. This kind of ‘discovering Toronto’ was fascinating to me.

We passed street art and the colorful Bohemian Kensington Market, where the people are as about as organic as you can get. Peter told us about this close-knit community and how they work together to keep things as untouched by modern commercialism as possible — no big-chain names, just locally owned and operated businesses.  I felt like I was getting a back-door pass to all that was Toronto! Places were pointed out to us that we would have never found on our own. And they’d never be listed on a top-ten list of things to see. But some of them should be!

Getting to know the people

Instead of being led to the big-ticket tourist attractions, I was learning about the people who live and have lived in Toronto along with their struggles and triumphs. Did you know that nearly half of all people living in Toronto now were born outside of Canada? There is so much diversity here.

We learned that the British originally worked out a purchase of the Toronto lands from the Mississaugas (the aboriginals) in 1787, but the deal was eventually rejected. Twice. It was not until 2010 when payment was finalized at $145 million.

When the Irish escaped to Toronto from the Great Potato Famine, they brought with them their distilleries and front-yard cabbage gardens. In fact, for awhile, Toronto was mockingly called Cabbagetown. The Irish neighborhood was also known as Corktown, either because of the concentration of people from County Cork…or from the breweries and cork-stopper manufacturers.

A stroll through Chinatown reminded us of the influence of immigrant workers who might have come to help build railroads but stayed and influenced Toronto, along with Jewish, Italian, and other ethnic groups.

Discovering Toronto and its Spaces

Walking through Yorkville taught us that when areas are revitalized, they often displace lower-income residents. It was difficult to fathom all the challenges that Toronto faces as a modern city.

Peter guided us seamlessly around Toronto — taking us to a rooftop bar to see fantastic views and then grabbing a cab to drop us off at the Beltline Trail, where we hiked under a canopy of trees so thick it was hard to remember we were in a metropolitan city. We ended up at the Don Valley Brickworks Park and Governors’ Bridge Lookout, where we enjoyed another spectacular view.

The story of the brickworks was so interesting! After fires destroyed much of Toronto in 1904, building out of bricks became crucial to Toronto’s survival. Good quality clay found near the Don River provided needed material for over 100 years. But now, the brickworks and quarry have been converted to park space and the abandoned buildings provide a community centre.

Nearly 13% of Toronto is public park and green space, twice that of Los Angeles and about the same as San Francisco. So while you might look at the skyline of Toronto as one huge line-up of skyscrapers, there is a lot of green tucked into its boundaries.

So Much MOre

Honestly, I can’t even begin to replicate all the experiences we had discovering Toronto. In about four hours time, we walked nearly 9 miles, talked about everything from Toronto’s history to how to orient yourself in Toronto (look for the CN tower — it’s always south), when to visit the Art Gallery of Ontario free, to where to find the best ethnic food. Peter answered all of our questions and gave us a great gift — a knowledge and affinity for Toronto we could have gained no other way. This small-group format was ideal for conversing and learning. It couldn’t have happened with a large tour group.

  • Book an Urban Expeditions Tour as the first thing you do in Toronto. It will help you so much, because you’ll be able to navigate better, and you’ll know what you want to do and where you want to spend more time after taking the tour.
  • Definitely bring that second pair of socks. Changing socks about halfway through the tour brings happiness to your feet!
  • Stay hydrated. Bring a water bottle. Urban Expeditions provides a snack/drink, but you’ll probably still need water throughout the tour.
  • Only with Urban Expeditions can you have your tour customized to what you most wish to
    Discovering Toronto

    A whimsical overview of Toronto

    see. You can choose from “pedestrian”, “arts”, “cultural”, or “green”…or you can request a customized combination of one or more of these elements. You’ll be asked what is most important to you. For me, I wanted to learn the history of Toronto, and I wanted good photo ops.

  • Guess what! Urban Expeditions has plans in the works to expand to San Francisco, Miami,  Seattle, Phoenix and Vancouver. There are also City Games you can participate in, in Toronto, Montreal, Ottawa, Kingston, Chicago and NYC.
  • A tour starts at $250 for three guests; that includes a personal guide for four hours, snacks, and all of your transportation. Grab a friend or two and become urban tourists! You can also purchase tickets through Airbnb at an individual rate.
  • Discovering Toronto

    Peter Odle, creater of Urban Expeditions

    Peter does not call himself a tour guide. Instead he’s a broker of practical local information. His specialty is transforming you into a local as quickly as possible! Discovering Toronto and sharing it with you is his passion.

So much gratitude to Peter for inviting my husband and I to experience an Urban Expeditions Tour. I am convinced there’s no better way to see a city than as an urban tourist!


Please share this pin!

Discovering Toronto


23 thoughts on “Discovering Toronto with Urban Expeditions

  1. Cindy Collins

    This sounds like a great walking tour and Toronto looks like an amazing city. The Beltline Trail hike sounds great I like hikes with a view at the end.

  2. Medha

    Sounds like you managed to visit some off beat places which is very cool. I’m still wondering why they asked you to bring the extra pair of socks lol. Incredible pictures by the way, so colourful!

  3. Anete

    Great tips for Toronto! It has been one of my top destinations for a while now, so I’m finally ready to visit it. I love the mention of roof top bar, as that is one thing that I always try to find in a new destination. Usually these are the best views of the town. 🙂 An Urban Expedition Tour really seems like the way to go.

  4. Ozzy

    Never even knew that Toronto had a walking tour. It is a wonderful read and could relate to it so easily and smoothly.
    The well spread greenery goes to show that the city must feel quite fresh.
    Thanks for a wonderful post.

  5. Sol Solntze

    What an excellent way to get to know a city – being led about by a local. Tourist sights are fine, but I always want to know about the history of the place as a whole and people who live there. I’d take the tour like a shot. We’ve done one one of those urban games in Moscow – that was also a great way to find out of the way places and random interesting facts. Cool!

  6. Lori

    Bricks, booze, and bacon? If nicknames are accurate, Toronto sounds like a great place to explore. What an interesting tour to take – I love the in-depth look at the urban landscape, history, architecture, right down to the street art, without being tempted to look outside the city!

  7. Kevin Wagar

    What an awesome tour! I’ve called the Toronto area my home for almost 20 years now. It’s awesome to see some of it’s coolest spots being highlighted on this tour.

  8. Sandy N Vyjay

    Urban tourism sounds like a unique and innovative concept. I love the fact that it affords an opportunity to have an immersive experience of the place and discover facts that are lesser known. I think that Toronto must have been quite a different experience this way and I am sure that would be the case for any other city too. The hidden gems of Toronto that you discovered are really fascinating. I really liked the trip to the university

  9. Cat

    Wow Peter brought you to some neat places! Even though I traveled to Toronto quite often, I definitely learned some interesting history (e.g., the cabbagetown). One of the areas I love walking around is the University of Toronto. So many historic buildings there!

  10. Victoria

    Omg loved this post! We were only in Toronto for a day and did a good tour in kensington market and it was so fun! These other areas are amazing and we would love to visit Toronto again soon!

  11. Liliane Fawzy

    You definitely saw lots! I love Toronto (biased as it’s my hometown) and I would have added the Scarborough Bluffs and Distillery District to this list as well as the beaches. I think the main issue I have with Toronto tours is that they’re incredibly focused on downtown. Toronto’s a huge city, there’s lots to see outside of the downtown core.

  12. Kate Rebel

    Cool, I love Toronto! I didn’t do a city tour while I was there but I still got the chance to explore the city quite well. I loved the Distillery District (so much brick!!) and Kensington Market a lot 🙂 I’d love to go back there and explore even more!

  13. Eric Gamble

    Love all of that grafitti art. I only had about 6 hours in Toronto and mainly spent time around the harbor and went to check the CN tower but obviously I need to go back and explore more of the local experiences and neighborhoods.

    1. Tami Post author

      Like any large city, Toronto offers so much! I could go back again to see more, and I was there for two whole days!

Make my day and leave a comment!

This site uses Akismet to reduce spam. Learn how your comment data is processed.