The shiny new Union-Pearson Express will get you from Pearson Airport (YYZ) to Union Station in 30 minutes. Take this time to charge your phones and get in a quick catnap.
You’ve already seen your first Toronto landmark: Union Station. Look across the street and you’ll see the York Hotel. Once the tallest building in the British Empire, it’s still quite charming and an excellent place for high tea or a drink.
Now, look down the street to the West. There’s the CN Tower. Is it worth it to pay to go to the top? Not in our opinion, but it’s really up to you. Toronto does have a dearth of rooftop bars with any height, so there’s no competition in terms of a good view.
Walk north on Bay Street. You’ll pass the Design Exchange and Hudson’s Bay. Stop for your obligatory selfie with the TORONTO sign in Nathan Phillips Square in front of New City Hall (and across from Old City Hall).
Unless you need to hit the Apple Store, walk through Nathan Phillips Square and around the back of City Hall to take the pedestrian walkway leading to the Church of the Holy Trinity and Eaton Centre. Here’s your chance to make the most of a favorable exchange rate.
Assuming you made it out of the mall, you’re now on Toronto’s little theatre row on Yonge Street. Pop onto Shuter Street to see Massey Hall and the newly renovated St. Michael’s Basilica. Head back to Yonge to make your way to Yonge-Dundas Square.
Now, you have three choices:
- Head to the ROM or Bata Shoe Museum
- See Toronto’s old town and the Distillery District
- Check out where real Torontonians hang out and shop
If you want to get some arts and culture, hop on the subway at Yonge-Dundas Square and take it south to Union Station and the University Line. Get off at Museum Station and you’ll be right there. The Royal Ontario Museum can easily fill the rest of your time, but there’s always the Bata Shoe Museum if that’s more your style.
To get back to the airport, get back on the subway at St George Station and get off at the Bloor GO station to transfer to the UP Express.
If you want to see old Toronto, head a block east from Yonge-Dundas Square and turn down Bond Street. Here you’ll find the MacKenzie House Museum, which is just up the block from St. Michael’s Cathedral and across from the Choir School. Head another block south and you’ll discover Met United.
If you’re ready for lunch or a cocktail, Carbon Bar shows a peek into Toronto’s industrial past. Otherwise, head a block east to Church Street, which will lead you to the Cathedral Church of Saint James. Relax for a moment in St James Park and enjoy the view of St Lawrence Hall before heading across the street and through Market Lane Park.
This deposits you directly in front of Saint Lawrence Market. Look west down Front Street to catch a great view of downtown with the Flatiron Building in front and the financial district’s skyscrapers behind it.
Turn away from the Flatiron building down front street to head to the Distillery District. While there’s no longer an active distillery there, it does have a brewery, which is an excellent spot to refuel.
To get back to the airport, walk out of the Distillery District to Cherry Street to the Distillery Loop Station. Catch the 514, which will take you for a lovely streetcar line along King Street. Hop off at King and Bay to get back to Union Station and catch the UP Express.
If you want to stop for some Japanese cheesecake, dim sum, or doner kebab, you can walk west on Dundas to stop at Uncle Tetsu’s or any number of delicious options on the way to Chinatown. Otherwise, take the 505 streetcar down Dundas to Spadina Avenue.
Cross so you’re on the west side of Spadina and walk up to Baldwin Street (once famous for being home to Toronto’s community of draft dodgers). You’ve made it to Kensington Market and if you’re lucky, you’ll be here on a car-free day. Baldwin, Augusta, and Kensington are all full of boutiques, cafes, coffee shops, and other neat spots.
When you’ve had your fill, head back to Spadina and walk down to Queen Street West, which is the next major intersection. If you’re big on music, you might want to cross east to see the Horseshoe Tavern. There’s plenty to see in both directions, but you should head west towards Trinity Bellwoods Park.
Once you’re past Trinity Bellwoods, you can head north on Ossington or continue on West Queen West to the Drake Hotel. If you choose Ossington, be sure to stop at Bellwoods Brewery.
To get back to the airport, catch the 505 streetcar from Dundas and Ossington and take it to Dundas West Station. Switch to the UP Express at the Bloor GO Station about a block east.