Your tour begins with a stroll past the Ontario College of Art and Design towards Queen Street West, the epicenter of youth culture in Canada in the 1980s. MuchMusic, Canada’s answer to MTV, opened here in the early part of the decade, quickly making the surrounding neighborhood a magnet for young people who wanted to see and meet their favorite bands. We will make a beeline for So Hip It Hurts, the oldest skateboard and snowboard shop in Toronto. Here, you’ll see the celebrity wall filled with the photos of actors and musicians who have shopped here, including Adam Sandler, Jack Johnson, the Beastie Boys and Robin Williams. The store has seen a lot during its 25 year lifespan; we will chat to the staff about the challenge to stay relevant as trends change and gentrification occurs all around them. Even if you don’t skate or snowboard, this is still an unmissable city stop.

For the best souvenirs and gifts in town, Spacing Store is where you want to be. Located at the 401 Richmond Building in a former industrial space turned into art galleries, this is the unofficial gift shop of Toronto, filled with products that were made in the city and/or feature local imagery and inside jokes (ask your guide what a ‘trash panda’ is!). The store arose out of a publication called Spacing, created in 2003 to report on issues such as urban design, sustainable development and public art, which the founders felt were not being sufficiently covered by the local media. We will talk with the staff and learn how this building was recently saved from closing after land tax rose significantly in the area.

Time for a beer at the legendary Horseshoe Tavern. We will sit close to the stage that has hosted acts like Willie Nelson, Loretta Lynn, Conway Twitty (it started as a country bar), The Rolling Stones, The Ramones, Nickelback, The Strokes, The Police and Barenaked Ladies, since the tavern opened in 1947. Oh boy do the bartenders here have stories! And we’ll hear some as we sip our beers. Prepare to be transported back in time.

In many cities around the world, graffiti inspires controversy but in Toronto it’s become part of the landscape and an accepted way of expressing yourself. Graffiti Alley is our next destination, where we will admire some of the best and most varied street art in the city. If we’re lucky we will see one of the street artists at work. Designs can be elegant, abstract, eerie or even fantastical, but there is no denying that this is art. Grab some non-toxic chalk spray and leave your own (temporary) mark on this famous walkway. Don’t forget to take a #selfie! 

Trendy Queen Street West is not just a shopping paradise but it also happens to be the world’s first Business Improvement Area (BIA). Founded in Toronto way back in 1970, these public/private partnership models have been copied by cities all around the world. Your guide will talk about how the local BIA has helped this neighborhood become one of the most successful and popular places to live, work and shop in the entire city. If the weather is good, we’ll stroll through Trinity Bellwoods Park, a popular hangout during the warmer months. Keep an eye out for the legendary white squirrels that live here; spotting one is supposed to be good luck!

What is Canadian food? Stop by Montgomery House Restaurant to chat with the chef, Guy Rawlings, about what constitutes Canadian cuisine and taste some of his seasonal specialties.

Toronto’s upcoming hippest neighborhood (you heard it here first!) is next. Ossington Avenue is full of vintage shops, ice cream parlors and restaurants galore, plus plenty more graffiti-filled alleys. We’ll browse the windowfronts and talk more about gentrification.

After an afternoon of exploring, we’ll make our final stop at Sweaty Betty’s for a relaxing drink. Don’t let the tattoos or piercings of some of the staff or patrons scare you off; although this is a local dive bar, it’s a welcoming one. It’s small, dark and cozy, with a great patio in the back. We recommend that you try one of the off-menu drinks that you have to know about to order!

After the tour, you may want to check out some places for dinner, including the new restaurants that have popped up nearby on trendy Ossington Avenue, or neighborhood favorites like the Golden Turtle. Another memorable option is the historic Lakeview Restaurant, whose 1950s retro style has featured in many movies and TV shows, including the 2017 Academy Award-winning film 'The Shape of Water.'

New York Times Reading List: 

• The Passions of the Butter Tart
• Shivering? That’s for City Folk. For Islanders, Ice Time Is Play Time
• Canadians Brace for Cultural Changes as Marijuana Becomes Legal
• 1 Neighborhood. 24 Kindergarten Classes. 40 Languages. (Some Miming Helps.)
• We’ll Never Be Royals, But ...
• How Immigrants Become Truly Canadian: On the Ski Slopes

A City Tour gift certificate is the perfect present for any occasion. Select a specific tour and date, or choose the value and let the lucky recipient decide how to redeem it.