Sports, Street Skateboarding, Economics, History & Culture

Overview

Available languages

English

1 hour 30 minutes

Mobile ticket

Discover the vibrant history, culture and economics of downtown Toronto on this unique walking tour. Explore Nathan Phillips Square and the iconic Toronto Sign, learn about the history behind the PATH and its post-pandemic recovery, and uncover the legacy of the Suites TV Show and Meghan Markle. Learn about the history and evolution of street skateboarding in Toronto and visit Brookfield Place. The tour also highlights the Toronto Raptors' 2019 NBA Championship and the NHL's Legends Row at Scotiabank Arena, offering a comprehensive glimpse into the city's sporting heritage.

- Guided walking tour through downtown Toronto, covering key attractions.

- Explore Nathan Phillips Square and the Toronto Sign.

- The only walking tour that covers the history of street skateboarding in downtown Toronto.

- Learn about the history of the PATH and how it has adapted to a post-pandemic world.

- Visit Scotiabank Arena to see the NHL's Legends Row and learn about the Raptors' NBA Championship.

Additional Info

Infants and small children can ride in a pram or stroller

Service animals allowed

Public transportation options are available nearby

Specialized infant seats are available

Suitable for all physical fitness levels

Cancellation Policy

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

What To Expect

Nathan Phillips Square

Travellers will learn about the history and present of Nathan Phillips Square, how it hosted the largest event in Canadian History and the famous Toronto Sign located at the ice rink.

Admission Not Applicable

Bay Street Corridor

Travellers will learn about the TV show "Suits" lobby location, and Prince Harry's now wife, Meghan Markle, who starred as a paralegal on it and her encounters with the press, fans, and safety while filming at the location. In addition, it will cover other film productions that have been filmed at the location, and talk about the challenges Toronto's film industry faces now.

10 minutes • Admission Not Applicable

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.

Gratuity/Tip

Options

Sports, Street Skateboarding, Economics, History & Culture

Reviews

5.00

13 reviews

Total reviews and rating from Viator & Tripadvisor

Terrific Experience!
S474BAmelc,,Dec 6, 2025
- Review from Tripadvisor
5.00
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!
Get an absolutely unique and entertaining view of Toronto during this tour!
G3974YRlyndam,,Dec 5, 2025
- Review from Tripadvisor
5.00
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.
A Fun Walk Through Downtown
J2513INjant,,Nov 24, 2025
- Review from Tripadvisor
5.00
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!
Eye Opening
705ankitr,,Nov 11, 2025
- Review from Tripadvisor
5.00
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.
Highly recommend!
392yilins,,Nov 11, 2025
- Review from Tripadvisor
5.00
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!
New perspectives on my own city!!
teosecara,,Nov 7, 2025
- Review from Tripadvisor
5.00
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!
A deeper visit
16kirkg,,Nov 6, 2025
- Review from Tripadvisor
5.00
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.
A Unique Way to Explore Toronto
shuminl2024,,Sep 9, 2025
- Review from Tripadvisor
5.00
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!
An interesting experience.
monicasE2991IA,,Sep 8, 2025
- Review from Tripadvisor
5.00
Duncan was a wonderful guide — friendly, informative, and full of fun local anecdotes. A good way to experience a piece of Toronto!
New discoveries
annmN6508RX,,Sep 7, 2025
- Review from Tripadvisor
5.00
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.