Toronto isn’t exactly known as “the city of romance”, but that doesn’t mean there aren’t plenty of romantic places just waiting to be discovered.

The city during the warmer months has lots of picturesque parks and rooftops to whisk your date off to. 

Not to be outdone, the colder months will have you cuddling up together in front of a fireplace at one of Toronto’s charming bars—or even laughing as you both attempt to navigate a crazy snowstorm. 

My boyfriend and I and I have found that no matter the season, Toronto has plenty of opportunities for romance. 

This list of the most romantic things to do in Toronto is inspired by dates we’ve had throughout our time here, plus a few bucket list items.

1. Explore Toronto Islands

Recently, I convinced Dean that we needed to spend the day exploring the Toronto Islands, which had just re-opened after COVID-19. It was one of the first full days that we had been out of the apartment exploring in a long time. 

Take a page from our datebook and plan a picnic near the beach. After lunch, rent some bikes and explore the island. If you’re feeling adventurous, opt for a tandem bike. It provided a lot of laughter throughout our day.

2. Journey to the Past at Casa Loma

You’ll spend the day wandering around the manor learning about what life was like in the early 1900s. 

Casa Loma is stunning—it felt like we were at Downtown Abbey. I highly recommend making a reservation to have supper in the garden after your tour—the gardens are lovely!

Fair warning, it gets cheesy when you get to the tunnel and stables—they’re decorated with a ton of tacky dragons and projections.

They use these during their game nights, but to be honest it ruins the romantic vibe (unless you’re really into Dungeons and Dragons).

3. Eat Your Way Through St. Lawrence Market

If your date’s a foodie, then look no further than this little market. They have booths galore, all  filled with the best meats, cheeses, seafood, and produce that Toronto can offer. 

You’ve got two options when you go here: either get groceries and cook a romantic meal together at home or indulge in everything you see that’s available to eat on the spot.

Dean and I went for option two and were in heaven. Stop by the oyster booth in the back of the marketplace—they shuck them for you on the spot and have a little counter that you can enjoy them at.

4. Have a Thrill at Canada’s Wonderland

Did you know that exciting and dangerous situations can lead to sexual attraction?

Take advantage of this research, and plan a trip to Canada’s largest amusement park. You can both bond over the anxiety and rush of riding one of the park’s many roller coasters.

Just plan dinner after the park, you don’t want to throw up on your date. 

5. Eat in the Dark at O.Nior

Imagine connecting to your partner only through touch and sound—it forces you to focus on them in an entirely new way. 

At O.Nior the aim of the restaurant is to make you understand what it’s like to be blind—in fact, their staff is blind. 

It’s a sensual experience that will leave you hanging on every word and touch from your partner. Just wear dark clothing in case you spill something—I can testify that it’s easy to knock over wine in the dark.

6. Gaze at the Stars

David Dunlap Observatory is an impressive and unique date spot—you and your date can gaze into the heavens using their state-of-the-art telescope. 

Make sure you pick a night with clear skies in the forecast. When Dean and I went, we could see Mars, Andromeda, and Jupiter. 

Fun Fact: They discovered the first black hole at this observatory.

7. Check Out Some Jazz

Is there anything sexier than a date at a jazz bar?

Imagine candlelight, cocktails, and the sound of jazz. You sit close to your date and listen as the music carries you away. Maybe you venture a touch or kiss as you get swept up by the music. 

There’s something primal about jazz music. It’s definitely not a first date kind of plan—wait until introductions are out of the way.

When you find that special person to take to listen to jazz, these are the places to look into:

The Rex: This place is historic and has a great atmosphere. It’s grungy, but that adds to its personality. It’s not the best place for food, but that’s okay because you’re there for the fantastic jazz and blues bands that they book. 

The Reservoir Lounge: This place is in the basement of a building from the 1800s. It has a sexy vibe complete with candlelight and dark corner booths. They make great cheese boards and have lots of delicious cocktails.

8. Laugh at Some Comedy

Research shows that couples who laugh together have a stronger bond than those who don’t—so comedy clubs make the perfect date spot.

Toronto is a city known for comedy—specifically, The Second City Comedy Club. It’s an iconic club that’s fostered comedy legends like Gilda Radner, Catherine O’Hara, Martin Short, and Mike Myers. 

Dean and I spent many a date night here while in the city. Every show we saw was original, funny, and well-acted. I highly recommend making Second City a date night priority.

9. See a Film at TIFF Lightbox

If your date’s a movie buff, take them to the TIFF Lightbox Theater to see one of the latest Indie films.

TIFF stands for Toronto International Film Festival—so bonus points if you score tickets when the actual festival is going on. 

The films are always well-curated, so you’re almost guaranteed to see something that will leave your date impressed.

10. Catch the Sunset From CN Tower

Begin your date by rocketing to the top of CN Tower in their famous glass-fronted elevators—seriously, you’ll travel 15 mph to get to the top in 58 seconds.

Maybe you feel like taking a walk on the wild side once you’re up there?

What is this “wild side” that I speak of? 

The famous CN Tower EdgeWalk! It’s the world’s highest full circle, hands-free walk. You and your date will stroll around the ledge of the tower’s main pod—1168ft above the ground!

If you’re looking for something less wild to impress your date, then make a reservation at 360. It’s the tower’s restaurant with the most romantic view in the city.

11. Hang Out in the Distillery District

The Distillery District is a charming village of industrial buildings, with brick-lined streets. It’s got a theater, plus lots of little shops and restaurants. 

My advice is to look ahead to see what’s on their special events calendar. When we went they had a giant holiday lights festival going on. You can also see if SoulPepper Theater Co. (the local theater) has any productions playing.

There are tons of delicious restaurants to check out. We ate at Madrina Bar y Tapas and really enjoyed it—especially the Truffled Egg Yolk dish.

I also highly recommend indulging in an after-dinner espresso martini—it’s especially delicious and potent with a layer of alcohol-infused whipped cream on top.

12. Head to a Rooftop Bar

As long as it’s not freezing out, rooftop bars almost always guarantee romance in the air.

These are some more romantic rooftop options to look into:

The Broadview Hotel: The service, music, and vibe here are all outstanding—plus it has an incredible view of the lake and city. If you like gin, give the Cucumber Mint Gin Splash a try—it’s refreshing on a hot summer day. 

Gusto 101: Except for a few pieces of decor, you’d never guess this used to be a car garage—it’s got such a cool vintage atmosphere. The pizzas and pastas are delicious—especially the mushroom pasta. 

Pauper’s Pub: Don’t let their name fool you, this isn’t your typical pub—they have an eclectic menu, beautiful views, and great vibes. The signature cocktails are delicious, especially the Mint Cucumber Mojito.

13. Catch a Show at the Ed Mirvish Theatre

If you know me even a little, you know that I’m in love with going to the theater.

There’s something magical about being transported to another place as the lights go down and the action begins—plus, it’s the perfect opportunity for some hand-holding and cuddling with your date (assuming things are going well). 

The Ed Mirvish Theatre has been bringing quality Broadway tours to Toronto for years. It’s a stunning historical venue that has a romantic old-world feel to it.

Just plan ahead on this one, especially if you’re trying to get into Hamilton.

14. Sing Your Hearts Out

You can tell a lot about a person based on their go-to karaoke song—so it’s the perfect way to learn more about your date. Head to Toronto’s Koreatown for some quality karaoke time together at one of these popular spots:

Freezone Karaoke: This place is a tad dated, but is a mainstay in the Toronto Karaoke scene. Their catalog has lots of classics from the ’90s and ’00s. They let you bring your own non-alcoholic drinks and snacks and also have alcoholic drinks available.

Echo Karaoke: This spot is trendy, they have a large song list, and the staff is sweet—what more could you want? They also have a solid drink list—just eat beforehand as they don’t have any snacks. One important thing to know is that they don’t accept cards, so bring cash!

15. Soar to New Heights Together

Why not make it one of the most epic dates ever by seeing Toronto from a bird’s-eye view with a plane or helicopter ride?

For the adventurous couple, a helicopter ride is the way to go. Check out Helitours, they offer private helicopter rides over the most popular spots in the city. 

For those who prefer a smoother ride, check out BreakAway Experiences. They specialize in romantic sunset flights over the city.

Their packages include a bit of champagne before the flight—I have stars in my eyes just thinking of all the romance that will be in the air.

16. Wander in the Botanical Garden

Okay, first make sure your date doesn’t have allergies—if they don’t then the Botanical Gardens are the perfect spot to get to know each other better. 

Just imagine strolling hand in hand with your special someone—through paths filled with blossoming flowers, a relaxing stream, and even a little waterfall. Bonus points if you pack a picnic to enjoy on the lawn.

17. Hit the Ice Together

If you’re in the city during the winter, then ice skating is a must. After skating, you can warm up together with cuddles and hot drinks somewhere nearby. 

These are some of the more popular rinks in the city:

The Bentway Skating Trail: This is the coolest rink around—it’s located under the concrete trestles of the Gardiner Expressway. Plan ahead and go on a Friday night when they have DJ’s playing all the greatest hits. 

Harbourfront Centre: Located right next to Lake Ontario, this spot is popular with tourists. They host DJ’d skate nights every Saturday. 

18. Amuse Yourselves at a Museum

Toronto is not lacking when it comes to museums—I was seriously impressed by a lot of them. These are some spots Dean and I really enjoyed visiting:

Art Gallery of Ontario: Also known as the AGO, this museum has lots of cool exhibits—including the coolest mirror room installation by artist Yayoi Kusama—it’s a must-see!

Thomas Fisher Rare Book Library: Okay, so technically it’s a library and not a museum, but it will impress any bibliophile—they even have Shakespeare’s First Folio!

The Royal Ontario Museum: Dean and I really loved their dinosaur exhibits—it even reminded us of a smaller version of New York’s Natural History Museum.

Bata Shoe Museum: This is a must if your date is a lover of fashion—their shoe collection puts Carrie Bradshaw to shame. I had to talk Dean into this one and after going, he agrees—even if you aren’t a major fashion lover, the history behind the footwear across different civilizations and cultures will hold your interest.

Aga Khan Museum: They have a romantic garden area that’s serene despite being in the middle of the city. The museum showcases the art and history of Iran, Turkey, and India. Plan ahead and book a reservation at Diwan, the museum’s highly rated Middle Eastern restaurant. 

19. Hit Up a Hockey Game

Hockey is the ultimate Canadian sport—they just love their ice skating, don’t they?

I admit I know very little about hockey (and have yet to attend a game) but even my mom has become a hockey fan over the last few years after attending her first game. She tells me the fun is in the food, company, and the yelling.

This definitely isn’t for everyone, but it’s a fun way to let loose with your date (if they like sports and/or yelling).

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

20. Check Out Art Battle

I bet you’re wondering, “what is an art battle?”

It’s a timed competition between multiple artists, with the crowd choosing the winner. 

The artists all get 20 minutes to complete their masterpieces.

The crowd votes on the winner—which likely will provoke a lot of conversation and debate with your date.

We both had strong opinions on whose pick was more talented. We even made the competition more interesting and bet on who would pick the correct winner—loser buys drinks!

21.  Sail Off Into the Sunset Together

There’s something so magical about being on a boat, especially at sunset with the skyline in the distance. 

Assuming the temperature is preferable, plan an afternoon learning how to sail with Gone Sailing Tours

When Dean and I went, we ended up sailing on a boat named the Australian Kiss—how appropriate is that? For those of you not in on the joke, Dean is Australian. 

This may have been one of my favorite dates while we were in the city. We sailed around the Toronto Islands and cruised around the harbor at sunset. The views of the city were out of this world!


I’ve found that Toronto is more romantic than I ever gave it credit for—though getting to experience the city with Dean added to the romance factor (even during COVID19). 

The city has plenty of opportunities for romance with your special someone, all you have to do is plan a bit. I hope this list helps you find the perfect date night activity for you and your date. 

I know we will always hold our memories of Toronto close to our hearts. It’s a city we’ll always smile about as we remember all of those fun days and romantic evenings that we shared. 

Have you found something romantic in Toronto that I’ve missed? Comment below!

Check out some of these popular and romantic Toronto tours!


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