I never imagined that I’d be spending most of 2020 in Toronto

To be honest, it wasn’t even on my travel bucket list.

It’s a city that my ex-boyfriend Dean moved to after his U.S. visa expired because of its proximity to New York.

I spent the first three months of 2020 traveling back and forth between NYC and Toronto on weekends. 

The plan was that we’d depart Canada in March to travel the world together for the next year.

Because of COVID-19, we ended up sheltering in Toronto as the world shut down. It forced our dreams of traveling the world to remain just dreams for this year.

I can speak for both of us when I say that Toronto now holds a very special place in our hearts. 

The city is vibrant, and the people are friendly. The museums, restaurants, and the overall vibe of this city is unique.

Based on our time exploring the city, and recommendations from locals, I’ve found these are the best things to do in Toronto.

1. Head to the Top of CN Tower

The CN Tower is the star of the Toronto skyline. Visiting the top of the tower offers incredible views, especially from the world’s highest glass paneled elevators.

They even offer an EdgeWalk experience—you get to take a walk along the exterior and hang off of the edge of the tower!

If you’re not one to walk on the edge, consider booking a reservation at their restaurant—it’s got a 360-degree view of the city.

Fun Fact: CN stands for Canadian National, the railway company that built the tower in 1976.

2. Hang Out in the Distillery District

Dean and I loved the time we got to spend in the Distillery District. It’s a tiny village of brick-lined streets and industrial buildings.

We spent the day walking around enjoying all the little shops that line the streets. Then had dinner before catching a play at the SoulPepper Theater Co.

If you’re craving a great cocktail and snack, head to Madrina Bar y Tapas. The Truffled Egg Yolk dish is also a must-try.

We also enjoyed their Espresso Martinis served with boozy whipped cream on top—be careful they sneak up on you!

3. Kayak on Lake Ontario

If you’re visiting during the summer, you must go kayaking on Lake Ontario.

The view of the skyline from the water is my favorite way to view the city, especially at sunset.

Check out Harbourfront Canoe and Kayak Center for easy rentals. They even offer paddleboards if you’re feeling adventurous. 

4. Catch a Hockey Game

I’m pretty sure it’s a crime to visit Canada and not see a hockey game.

Canadians take this sport very seriously—they even have a hockey display at the Royal Ontario Museum.

I admit Dean and I didn’t make it to a game before the shutdown, but it’s on our to-do list for when we return.

I have a feeling that these games are entertaining with all the hardcore fans.

Pro-Tip: The local team is the Maple Leafs, so bring some blue and white to wear to the game.

5. Head to the Hockey Hall of Fame

If you find yourself a fan of hockey, then go to the Hockey Hall of Fame to see the infamous Stanley Cup. 

There’s tons of memorabilia, interactive exhibits, and an impressive trophy room.

Plus, you get to take a photo with the holy grail of hockey, more commonly known as the Stanley Cup.

6. Roam Around Casa Loma 

I never expected to find a castle in the middle of Toronto—okay, technically it’s a Gothic-style mansion, but trust me it has major castle vibes.

Once you pay admission, you’re free to wander around the mansion (they offer audio tours).

You’ll learn all about the Pellatt family who built the (at the time) largest private residence in Canada.

I loved seeing all the beautifully decorated rooms—it felt a bit like being at Downtown Abbey.

It was interesting reading all descriptions and histories on each room. The family even built a tunnel that runs from the primary home to the hunting lodge and stables across the street.

Casa Loma oozes history and romance until you get to the tunnel and stables. They put up cheesy medieval dragons and weird projections in both the tunnel and stables—apparently these displays are for their themed interactive escape room games.

7. Check Out Kensington Market 

This bohemian market is funky, charming. The market offers plenty of vintage shopping, hip coffee spots, and cool little bars.

My favorite is all the food stands —seriously, all the unique food available will make your head spin.

If you’re a cheese lover like me, then head straight to Global Cheese. They have an incredible selection of cheese to sample.

I fell in love with their raw milk cheese selection—un-pasteurized cheese is heavenly but unfortunately banned in the U.S.

The market is open year-round, though winter can get cold enough to make the market lose some of its charms.

Pro-Tip: Most booths accept credit/debit cards but have some cash on you. 

8. Check Out the Thomas Fisher Rare Book Library

Are you looking for a unique experience in Toronto that’s free?

Well, this is it.

The library holds Margret Atwell’s original hand-written draft of The Handmaid’s Tale, and Shakespeare’s First Folio from 1623 (naturally, I geeked out over that beauty). 

It’s a book lover’s dream—they even allow you to request books from their collection to read in their reading room.

The interior of the library is stunning, check it out—it’s the perfect place for a beautiful Instagram photo.

9. Laugh It Up at Second City 

Second City is a Toronto institution known for its improv and sketch comedy.

It launched the careers of comedy legends like Gilda Ratner, Dan Aykroyd, Catherine O’Hara, Martin Short, Mike Myers, and John Candy.

This is a place that Dean and I loved to include as part of our date nights.

Every show we went to was funny, original, and well-acted. I highly recommend going to the Second City for a night of comedy.

10. Browse the Bata Shoe Museum

This museum is like Mecca for shoe lovers. It astounds me that New York is lacking a museum like this with its Sex and the City history.

They have 3 floors of shoes on display—Carrie Bradshaw would be in heaven!

Bata Shoe Museum examines the history of footwear across different cultures and civilizations.

Their displays range from indigenous shoes to Elton John’s eye-catching footwear.

If you’re like me, you’ll definitely walk out with a craving to go shoe shopping. 

11. Check Out an Art Battle 

I’m obsessed with Art Battle, which is live competitive painting in front of an audience.

Basically, artists get 20 minutes to create their masterpieces. While they work, the audience wanders around the space watching their creative process.

At the end of the 20 minutes, the audience votes on the winning piece of art.

This is easily one of the unique events that I’ve ever encountered. I hope this catches on and becomes something done in other cities.

12. Scream at Canada’s Wonderland

What is Canada’s Wonderland, you ask?

Well, it’s only one of the biggest amusement parks in Canada.

I didn’t get a chance to go, but locals tell me it’s a fond part of any Torontonian’s childhood. The Yukon Strike, Behemoth, and Leviathan are the rides locals say you shouldn’t miss.

Local’s Tip: The funnel cake at this place is “incredible” according to one of the locals we met.

13. Go “Skydiving”

At iFly Toronto you can “skydive” in one of those crazy air chambers.

This is a bit of a splurge for either 2 minutes for flying time for $81.36 or 4 minutes of air time for $119.99 for first-time flyers. 

Full disclaimer, I never got around to trying this, but it does look like a lot of fun.

14. See The Royal Ontario Museum 

I was really impressed with ROM’s many exhibits—it reminded me of a smaller Natural History Museum.

We spent most of our time there looking at all the dinosaur exhibits. The rock and mineral exhibit was also interesting, with tons of gorgeous gemstones to admire.

If you’re looking for an indoor activity, this is the place to pass a few hours. Plus, it’s down the block from all the fabulous shopping on Bloor Street, which is kind of like a mini 5th Avenue.

15. Eat at St. Lawrence Market

St. Lawrence Market is a must for foodies—it’s filled to the brim with local vendors offering delicious goods. 

Definitely check out the oyster stand—they shuck fresh oysters while you wait. The staff is friendly and knowledgeable, and the oysters are delicious. It’s one of my favorite spots that we discovered while in Toronto.

16. Check Out the Canadian Opera Company 

If you like opera, go to The Canadian Opera Company’s free concert series at the Four Seasons Center for Performing Arts. 

You’ll want to arrive early, it’s first come first served with no pre-bookings available. Most people I spoke with recommend arriving at least an hour early to get into the venue before it hits capacity.

17. Hit Up A Rooftop Bar

I love going to rooftop bars when I visit new cities, since they always have some of the best views.

Toronto is not lacking when it comes to beautiful rooftop bars. These are some of the most picturesque:

Lavelle: This might be one of the best views for that perfect Instagram photo of the CN Tower. I’d recommend going for a round of after-dinner drinks. Go to nearby Oretto for their truffle pasta and oven cooked pizza for supper—it’s heavenly!

The Roof at SOCO: This is another perfect spot to check out the CN Tower in all its glory. The only downfall is that it closes at 10 pm. Try their Dragon Fruit Sangria, it’s delicious!

Kost: Check out the sunset at this idyllic rooftop bar with a beautiful view. It’s a lively atmosphere and the food and drinks are amazing. Try the Calamari and Short Ribs while you’re there. 

18. Chester Hill Lookout 

Speaking of views, this little spot has a beautiful view of Toronto’s cityscape. It’s in a residential area of the city, making it the perfect non-touristy spot to watch the sunset. 

Check out the Instagram famous giant astrology wheel painted by one of Toronto’s all-star sidewalk artists Victor (@whatsvictorupto). 

19. Take a Bike Tour of Toronto Islands

Get in a bit of exercise with a bike ride while you explore the best of the Toronto Islands.

You can get to the islands by taking the ferry which runs every hour. The wonderful news is the islands are all connected, so you can walk between them once you arrive.

You can rent bikes on the island—we rented a tandem bike which proved comical to get around on.  

We explored both Ward’s Island Beach and Centre Island while we were biking. I recommend heading to Ward’s Island first and grabbing some delicious Greek food by the beach bar there. 

Then head to Centre Island for your bike ride. The views of the city skyline are stunning and perfect if you’re looking for a romantic moment.

If you don’t feel like biking, there are also several excellent boat tours available!

20. See Fort York National Historic Site

If you’re into history, then this is a must while you’re in Toronto.

Non-history buffs, here’s the deal: Fort York was a strategically important military site used by the British and Canadians during the American Revolution. 

They now have re-enactments, guided tours, and sometimes even fire off the cannon.

I spent a couple of hours wandering around the site, and learned a ton about the War of 1812. The staff was really welcoming and knowledgeable throughout our experience there.

The fort also offers art exhibits, cooking demonstrations, and sometimes even musical performances by Canadian artists. Just check their calendar for upcoming special events

Fun Fact: They have a WW1 front-line reenactor cat on premises named Private Julius.

21. Check Out All The Street Art

I’ve never seen a city with so much street art—seriously, it’s everywhere!

Check out Graffiti Alley on Rush Lane from Spadina to Portland Streets. It’s home to some of the best street art in Toronto.

Every time I walk by, I spot a few Instagramers trying to pose for the perfect graffiti selfie. 

If you’re like me and prefer to stumble upon things organically, don’t worry, everywhere you turn in this city you run into street art—all thanks to StreetARTToronto. They’re a program founded a few years ago that’s encouraged the developing street art scene. 

22. Catch a Show at The Ed Mirvish Theatre

Thankfully for me, Toronto has a happening theater scene. In fact, I saw my very first show ever (The Phantom of the Opera) when I was 5 years old in Toronto.

The Mirvish Theatre continues to bring Broadway tours into town and is a must for any theater fans.

Unfortunately, we didn’t make it to the theater this trip, but I’ll say going to the theater is ALWAYS a good idea!

23. Dine in the Dark at O.Nior

I know you’re thinking “how the hell am I supposed to see the menu to order then eat in complete darkness?”

The idea behind O.Nior’s concept is that the patron gets to experience what it’s like to be blind. The most interesting part is that it’s staffed by blind people.

First, you’re brought into a well-lit waiting area to order and learn how the experience will work.

Once you get used to the fact it’s pitch black, you quit trying to see things. You become more present and start using your other senses.

My biggest advice is to wear dark clothing in case you spill or knock something over, which is easy to do in the dark (I know because I spilled wine).

Oh, and in case you’re wondering, the food comes already cut up, so no need to struggle to cut your steak in the dark.

We had a wonderful experience here, and would definitely do it again as a date night.

24. See the Stars at David Dunlap Observatory

Get inspired and drawn to the heavens in the same place that discovered the first black hole. This place is such a gem and should absolutely be on your to-do list.

The volunteers and staff were wonderfully warm and kind while we visited.

The evening I went, I was lucky and had clear skies, meaning I got to view Mars, Andromeda, and Jupiter.

25. Check Out the Aga Khan Museum

This small museum showcases culture, history, and art from different Islamic countries including Iran, Turkey, and India. 

The museum has a beautiful garden area that’s so serene despite being in the middle of the city. I would love to just go hang out in the garden and read for a few hours.

I highly recommend checking it out if you’re into art history and culture.

Local’s Tip: Make a reservation to eat at Diwan, the museum’s restaurant. It’s a posh spot with amazing Middle Eastern food.

26. Go Sailing on Lake Ontario

I’m all about an afternoon or evening spent on a boat—especially one with a view.

While you’re in town, check out Gone Sailing Tours to experience the city from the water. 

We sailed through Toronto Islands and the harbor—the views were stunning, and the crew was knowledgeable, professional, and great to deal with.

27. Head to Toronto Botanical Gardens 

These gardens are the perfect spot to take a walk or cycle around if you need a break from the city. 

There are tons of beautiful flowers and trees, and lots of paved trails to wander around.

This is another spot I’d recommend bringing a book to sit and enjoy while out in nature.

28. See the City From Above

If you’re able to afford it, why not see the city from above, by booking a plane or helicopter tour of the city. This is something that’s sadly still on my bucket list.

Helitours offers private helicopter rides over some of Toronto’s most iconic buildings. Expect to see the CN Tower, Rodger’s Centre, and Ontario’s Parliament. 

If helicopters aren’t your thing, book a private plane ride with BreakAway Experiences. They specialize in romantic pre-sunset or sunset flights over the city’s iconic skyline. You can even book a package with them that includes some champagne. 

29. Go Ice Skating

Ice skating must be considered Canada’s national past-time with how much they love hockey.

Toronto has tons of spots to glide across the ice with the greatest of ease (unless you’re an untalented skater like me).

Locals have told me these are some of the most popular spots to spend time on the ice:

Harbourfront Centre: This rink is right next to Lake Ontario, making it a popular spot for tourists. Every Saturday evening they have DJ’ed skate nights.

Sherbourne Common: This is the perfect rink if you’re looking for a superb view of Lake Ontario and the downtown skyline. The rink is stylish and has won multiple architectural design awards.

The Bentway Skating Trail: This popular spot opened a few years ago under the concrete trestles of the Gardiner Expressway. They offer Friday DJ nights and have warming centers available created from old shipping crates.

30. Head to the Art Gallery of Ontario 

AGO has a model ship exhibit in their basement—how random and fun is that?

If you’re under the age of 25, then admission here is free. There’s a ton of Canadian art, and Inuit, African, European, and Oceanic.

My favorite exhibit is the mirror room by Yayoi Kusama—it’s a must-see!

31. Hang Out on The Waterfront 

If the weather is beautiful while you’re in town, then you must check out The Waterfront. It’s an area along Lake Ontario that’s peaceful and charming. 

I spent a lot of time walking along the paths in this area when I first arrived in Toronto. I love grabbing a coffee and watching all the boats in the marina.

Stop by the Music Garden while you’re strolling—it’s designed by Yo-Yo Ma in 1999 and inspired by Bach’s “Suite 1 in G Major.”

You’re almost guaranteed to hear someone playing music in this little area. Occasionally, I’ve even spotted guided meditations taking place there around sunset.


“The fact that over 50 percent of the residents of Toronto are not from Canada, that is always a good thing, creatively, and for food especially. That is easily a city’s biggest strength, and it is Toronto’s unique strength.”

Anthony Bourdain

No matter what you prioritize on this list, strike up some conversations as you explore the city. The people in Toronto are some of the friendliest that I’ve encountered while traveling. Most love to chat and I found they’re pretty much always happy to help you out.

And to back up the late, great, Anthony Bourdain, the art scene and foodie scenes are fantastic. One of my favorite things about living in Toronto this long is that I’ve been able to try so many restaurants. Dean and I have already been debating which local spots we’ll miss getting take-away from the most as our time here winds down.

I know that without a doubt, I’ll be back to spend more time in Toronto over the years. It’s a city that will forever have a special place in my heart.

Comment below, or e-mail me with questions. I’m always happy to help with recommendations!

Check out some of these popular tours and things to do during your time in Toronto!


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