Walk downtown Toronto with a guide who connects skateboarding culture, sports landmarks and the financial district in a compact 90-minute route. Expect architectural highlights, PATH history, and behind-the-scenes cultural context.
More ways to explore the area's outdoor wonders
The city arrives before you do — glass towers reflecting a bruise of sky, taxis carving lanes, and a plaza that pulses with civic life. Start at the west stairs of Nathan Phillips Square and you can already feel the itinerary: the Toronto Sign presides like a civic landmark that dares you to take a photo, while the square’s open concrete invites skateboarders and pedestrians into the same choreographed motion.
Difficulty
easy
Duration
1.5 hours
Fitness Level
Casual urban fitness — comfortable walking shoes and the ability to stand for brief stops
Wildlife
History
Nathan Phillips Square and the surrounding financial district grew alongside Toronto’s emergence as Canada’s economic center; the PATH developed to connect commerce beneath the city streets.
Conservation
Respecting public spaces matters: avoid littering on plazas and support small PATH businesses to help maintain the area’s vibrancy post-pandemic.
Reserve your spot on the Sports, Street Skateboarding, Economics, History & Culture today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Meet at the west stairs
Arrive 10 minutes early and look for the group at the foot of the west-side stage stairs in Nathan Phillips Square.
Wear grippy shoes
Streets and indoor marble can be slick; low-profile, grippy footwear keeps you steady while watching skateboard trick spots.
Carry a transit card
The tour begins and ends near major transit hubs — a PRESTO card or day pass speeds your arrival and departure.
Pack a small bottle
Ninety minutes of walking in summer or a busy PATH day can dry you out; bring a compact water bottle or refillable flask.
Comfortable walking shoes
Provides traction and comfort on pavement, steps and indoor floors.
Light rain jacket or umbrella
Spring showers are common; pack a compact layer to stay dry.
spring
Reusable water bottle
Keeps you hydrated during summer heat and while moving between stops.
summer
Transit pass or PRESTO card
Speeds arrival and departure since the route begins and ends near transit hubs.