Toronto: Weekender Guide

by Tegan

Toronto is a cosmopolitan and adventure-filled city, well-worth adding to your North America travel bucket list. Located just a short flight away from the mid-Atlantic and Northeast, Toronto is a great base to explore Ontario, as well as extensions by car or train to Montréal, Ottawa, and other Canadian gems.

Fun fact: Alex’s family is Canadian, and he went to high school there! We absolutely love Canada, and try to spend as much time there as we can. We’ve mainly concentrated our visits in Ontario– relaxing at the adorable family farm in Harwood, or hanging out with cousins and friends in Montréal, Port Hope, Scarborough, and beyond– but we’re dying to visit the central and western parts of Canada, and hope to do that soon. 

For us, no visit to Canada is complete without a day trip to our favorite quaint small town in the area, Cobourg, as well as hanging out on nearby Rice Lake, demolishing some butter tarts from Betty’s Pies, and drinking as many Ice Caps from Tim Horton’s as humanly possible. Canada overall has a much more relaxed vibe than much of the U.S., and while the winters can be a bit harsh, summer there is unbelievably beautiful. 

But if you’re visiting Ontario for the first time, you’ve got to spend at least a day or two in Toronto. Since we’ve visited so many times, we’ve put together the ultimate weekender itinerary for you. Enjoy!

Toronto Top 5:

  1.  Visit the Distillery District for a trip back in time to Victorian-era cobblestones and tons of fun fusion restaurants and window shopping.
  2. Visit an open-air market, like the St. Lawrence Market or the Kensington Market. Don’t miss the murals at Kensington! 
  3. Visit the splendid Royal Ontario Museum (ROM) for your dose of world-class art, or perhaps the Hockey Hall of Fame, if that’s more your speed.
  4. Check out Casa Loma and the University of Toronto campus for two doses of unbelievable Gothic architecture, right in the city.
  5. Shop til you drop at Eaton Centre, North America’s most-visited mall.


  1.  Toronto has a fantastic public transit system, that’s easy to use and will get you all around the city. The Toronto Transit Commission (TTC) has extensive bus, subway, and streetcar service that connects the whole city fairly seamlessly. If you’re staying in the center of the city, you can likely walk almost everywhere, but it’s great to take the TTC on those particularly chilly (or hot) days, or if you want to check out High Park or other areas outside the city center.
  2. As far as areas to stay in, we recommend looking for an Airbnb near The Annex or Yorkville areas. Both are very central and beautiful– The Annex has a more student-friendly vibe while Yorkville definitely has a more upscale vibe, but both are great. If you really want to be in the center of the action, you can book in the Entertainment District (where the CN Tower, etc. are) but we love staying in slightly cheaper and (in our opinion) a little less touristy areas. 
  3.  If you’re flying in, try to fly into the Billy Bishop Toronto City Airport. Budget airlines like Porter fly into here, as well as some larger ones– there’s a direct flight from Boston Logan that we particularly like! Trust us– it’s way better than flying into Pearson! Pearson, Toronto’s huge international airport, is located way out in Mississauga, while Billy Bishop is right next to Union Station, with a free (and frequent) shuttle service that drops you off right in front of the station, in the center of the action!  

P.S. I couldn’t resist adding this major throwback photo… from all the way back in 2015! We look like such babies! 

Toronto Weekender Guide!

Day 1:

Start your day with a coffee at Canadian standard Tim Horton’s! While this is definitely not high cuisine by any means, we love Tim Horton’s and grab a coffee here whenever we can when we’re in Canada! It’s definitely easy to be unhealthy here, with their wide variety of sweet treats… but they also make a surprisingly delicious latte. If you’re splurging, check out their iced cappuccinos, or Ice Caps. Tim Horton’s is as ubiquitous as a Starbucks or Dunkin’ in the U.S., so you definitely won’t have any trouble finding one. 

Next, check out the St. Lawrence Market in Old Toronto. It’s a massive open-air warehouse with 100+ vendors selling all sorts of goodies. 

The market is very close to the Distillery District, a recently-revitalized Victorian-era walking area. There are loads of fun restaurants, wine bars, and lovely public art to explore in this pedestrian-only area, one of our favorite parts of the city. The brick buildings were originally home to the largest whiskey distillery in the (then) British Empire. If you visit during Christmas time, the area hosts Toronto’s Christmas Market!

Also nearby is Sugar Beach and Harbour Square Park, as well as the access point to the Toronto Islands, Queen’s Quay Terminal. If you’re interested in visiting the Yacht Club, wildlife sanctuary, and beautiful scenery of Centreville and the Islands, inexpensive boat tours depart fairly frequently. We love walking around the Harbourfront area, especially after too many tapas at Madrina in the Distillery District! 

If you’re interested in visiting the Hockey Hall of Fame or the iconic CN Tower, they are both located close by back near Old Toronto. You can also visit the Old Toronto City Hall.

For dinner, check out Chinatown’s myriad offerings. There’s dim sum, buffet-style, and all sorts of mouthwatering eateries to choose from, and colorful Kensington Market is nearby, as well. We really love Rosewood Asian Cuisine, and recommend their lunch buffet dim sum! 

Day 2:

Start your day with a visit to the unparalleled Royal Ontario Museum, or ROM, in the northern part of Toronto. There are over 13 million artworks, archaeology, natural history, and cultural pieces in this mammoth museum, and it’s distinctive architecture makes it hard to miss! One tip– this museum gets very, very crowded. It’s a must-see attraction in town, so we definitely recommend arriving early. Child, student, and senior admission is available, as well as membership. We especially enjoyed the Gallery of Chinese Architecture and the Eaton Gallery of Rome. There is also a spectacular gallery dedicated to Canada’s First Nations people.

Next, take a stroll through nearby Queen’s Park, home to a beautiful green space as well as the imposing Legislative Assembly of Ontario and Ontario Provincial Parliament buildings. Nearby, explore the gorgeous Gothic University of Toronto St. George campus. The campus is breathtakingly beautiful, and you’ll feel like you’ve become the protagonist in a Regency novel. 

If you’re in the mood for a bite to eat, head over to nearby Yonge Street (pronounced Young.) Once considered the longest street in the world according to Guinness World Records, it’s a major artery filled with places to eat, shopping, and more.

In the afternoon, check out Casa Loma, just north of the ROM. This grandiose urban palace dates back to 1914, and is frequently used as a set piece for TV and movies, like X-Men. The attached gardens and stables are super gorgeous, too! 

Bonus: did you know that it’s really easy to do a day trip to Niagara Falls while you’re in Toronto?

Located less than 90 minutes away from downtown Toronto, this is a can’t-miss attraction if you have a car or the extra time. Niagara Falls is absolutely stupendous, straddling the U.S. border via the “Rainbow Bridge.” The largest/most famous section of the falls is the Horseshoe Falls area, but you can also check out various other viewpoints. The Niagara on the Lake area has fabulous vineyards, and there are also all sorts of hiking and biking trails to explore. 

Have you been to Toronto, or “The 6,” as it is affectionately called by locals? Let us know in the comments

As always, save this guide for later on Pinterest, below! And stay tuned for more Canada guides, to Montréal, Ottawa, more Ontario content, and more, coming soon!

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Daniella January 24, 2021 - 2:13 am

I haven’t been to Toronto yet (only the BC part of Canada). I loved the time I spent in Vancouver and surrounds and I think the country is incredibly beautiful so I definitely want to see the rest of it! Thanks for sharing this awesome guide!

Tegan January 24, 2021 - 12:13 pm

We haven’t made it out to BC yet and are dying to! Hopefully soon we can visit both! 🙂

Linhy January 24, 2021 - 8:06 am

My family is in toronto but never been to some of these places. Would have to see these places when we will be able to travel again. Love this post !

Tegan January 24, 2021 - 12:13 pm

Thank you! Here’s hoping we’re all traveling again soon! 🙂

hari January 24, 2021 - 7:26 pm

from your post, there are a couple of things I can clearly understand. Canada is a beauty filled country and Toronto is a great place to visit.
can’t wait to visit these places.
thanks for sharing this awesome post.

Robert January 25, 2021 - 9:32 am

We finally visited Toronto for the first time from BC couple of seasons again while on our Cross Canada Train Journey. Great City with so much to see and do! Really enjoyed St. Lawrence Market & Casa Loma. 🙂

Anabella January 25, 2021 - 7:24 pm

Hope we can travel soon and experience this beautiful city! Thanks for the tips!

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