Toronto Walking Tour: Explore Downtown Highlights

Uncover Toronto’s vibrant history and culture on a unique walking tour, exploring street skateboarding, iconic landmarks, and sports heritage.

Duration: 2 hours, 30 minutes
Cancellation: 24 hours
Highlights
  • Nathan Phillips Square - Visitors will explore the history and current significance of Nathan Phillips Square, known for hosting the largest event in Canadian history and featuring the iconic Toronto Sign at the ice rink.
  • Nathan Phillips Square - The tour includes a visit to the nearby Spirit Gardens, an Indigenous cultural space with…
What's Included
  • Travel Advising in Toronto - I will help travellers at the end with planning, and recommendations.
  • Google Map of Duncan’s Toronto Recommendations - Food, drink, and of course, dessert.
What's Not Included
  • Gratuity/Tip
Additional Information

Embark on a captivating walking tour through downtown Toronto, delving into its rich history, culture, and economy. Discover Nathan Phillips Square and the famous Toronto Sign, gain insights into the PATH’s history and its post-pandemic revival, and explore the legacy of the “Suits” TV Show and Meghan Markle. Uncover the development of street…

Location
100 Queen St W
Queen Street West
Please meet at the foot of the stairs to the stage that are on the west side of Nathan Phillips Square. I will be waiting for you on the stairs!
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(14 Ratings)
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1 star
S474bamelc
Dec 6, 2025
Terrific Experience! - Duncan gave an excellent tour, full of fascinating and little-known insights about the great city of Toronto. He was easy to understand, welcomed every question, and clearly cared about giving us a memorable experience. I wholeheartedly recommend this tour!
Review provided by Tripadvisor
G3974yrlyndam
Dec 5, 2025
Get an absolutely unique and entertaining view of Toronto during this tour! - Duncan brought an interesting and enjoyable perspective to learning about Toronto. I particularly liked the information he shared about the new Reconciliation Garden next to Nathan Philips Square. He also gave examples or told stories about each site which were educational or entertaining. His information about the law society building and its fence was a good example of his unique style. As well, his information about the financial area and the 2020 statue of the mesmerizing head sculpture was fascinating. Even his interesting stories about skateboarding in the city made his tour one-of-a-kind. This tour is absolutely worth taking.
Review provided by Tripadvisor
J2513injant
Nov 24, 2025
A Fun Walk Through Downtown - Duncan is a great tour guide. He's a local skateboarder with a deep knowledge of the city. The route he chose was well-designed and included plenty of hidden and overlooked art installations and buildings, as well as the famous PATH network. At the end, he provided a Google Maps map of personal dining recommendations throughout the city that was worth the price of the tour alone!
Review provided by Tripadvisor
705ankitr
Nov 11, 2025
Eye Opening - This was an awesome and informative tour of Toronto. Duncan has collected some interesting set of facts for place around Toronto that I didn't know even after staying here for almost 4 years. I would say it is worth it.
Review provided by Tripadvisor
392yilins
Nov 11, 2025
Highly recommend! - This tour was a fun way to learn about the core of Downtown Toronto. Duncan shared interesting facts, stories about the buildings and sculptures we passed, and personal anecdotes from growing up in the city. It was clear that he cares about his work and wants everyone to appreciate Toronto the way he does. I highly recommend this tour for both locals and visitors who want to explore and learn about this great city!
Review provided by Tripadvisor
Teosecara
Nov 7, 2025
New perspectives on my own city!! - As a Toronto native, I wanted to see my city from a new perspective, and Duncan’s tour exceeded my expectations. He shared unique and captivating insights about Toronto’s history, culture, and street life - his knowledge and passion for the city really shine through. I loved how engaging he was and how effortlessly he connected stories about local spots, people, and even the skateboarding scene to the broader culture of Toronto. He took me to places I’d never visited before, even after living here for years, and helped me appreciate the city in a totally new way. I’d highly recommend this tour to both locals and visitors, it's a great opportunity to have fun, learn something new, and take in some authentic Toronto energy!
Review provided by Tripadvisor
16kirkg
Nov 6, 2025
A deeper visit - I'm actually a Toronto native curious to get to know my city better and I definitely made the right call. Walking by the same buildings was actually very different with someone there telling you the background and stories of what this city is and how it all came together. So I really appreciate that Duncan! Duncan was fun, easy to understand, and a lot to share. Had a great time.
Review provided by Tripadvisor
Shuminl2024
Sep 9, 2025
A Unique Way to Explore Toronto - This tour was a fun and interesting way to learn some of Toronto’s more quirky and off-the-beaten-path facts. Duncan is a great guide — super friendly, funny, and genuinely wants everyone to have a great time. You can tell he loves what he does!
Review provided by Tripadvisor
Monicase2991ia
Sep 8, 2025
An interesting experience. - Duncan was a wonderful guide — friendly, informative, and full of fun local anecdotes. A good way to experience a piece of Toronto!
Review provided by Tripadvisor
Annmn6508rx
Sep 7, 2025
New discoveries - Duncan was very personable and knowledgeable about his subject. He showed me places I’ve never been to even though I’ve lived in Toronto for 30 years.
Review provided by Tripadvisor
From $11
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).