Pause outside the Hockey Hall of Fame, a tribute to Canada’s most iconic sport. See the “Spirit of Hockey” statue, capturing the grassroots origins of the game, and hear how legends like Tim Horton helped shape both hockey culture and one of the country’s most recognizable brands.

This is Toronto’s Flatiron Building, built in 1892, and yes—it’s older than the more famous one in New York. It was designed to squeeze into this awkward wedge of land, which makes it look like it’s about to slice through traffic like the bow of a ship. It belonged to the Gooderham family, who made their fortune in whiskey, so if the building looks a little confident… that’s probably why.

Berczy Park is one of Toronto’s most charming public spaces, tucked just behind the historic Flatiron Building. At its centre is the city’s most beloved fountain, featuring dozens of cast-iron dogs of all shapes and sizes, all gazing up at a single golden bone perched at the top. It’s a playful tribute to the neighbourhood’s dog-loving residents and a reminder that even in a busy downtown, Toronto still makes space for a little whimsy.

Learn about the centre of spiritual life for the rich and powerful in Toronto 100+ years ago at this Anglican cathedral. The fifth to stand here, the present building was completed in 1853, after a massive fire wiped out the centre of Toronto in 1849 in our first "Great Fire". It was the church of the first British colonists and stood as a symbol of power for the ruling class through much of the city's history. If the church is open to the public we will take a peek inside!

The bulk of this tour takes place in Old Town Toronto and your guide has a number of stories and sites to share with you. Toronto's history as a small military town established to support a nearby fort (Fort York - in the west end of downtown) and growth into a bustling city will be explained over the course of your time here.

National Geographic Traveller Magazine declared this the "best market in the world" several years ago and it's a must-visit for everyone exploring Old Town Toronto. Closed on Mondays (and civic holidays) this is a place you should schedule some time to visit more thoroughly after your guide gives you an overview of its history and significance to not only the early Town of York, but the modern Toronto that town became. Not only a popular tourist attraction, the St Lawrence Market draws locals in search of specialty and locally-produced items like gourmet mustards, Ontario wines and cheeses, and the famous peameal bacon sandwich. If you worked up an appetite on your walk because the food and drink offered at the St Lawrence market is the big finale. Taste a peameal bacon sandwich, a butter tart, a famous soft drink invented just blocks away, and more!