toronto date ideas

A dozen unique date ideas to try in Toronto this summer

Rediscover the city and your relationship with this fun-filled guide

After months spent self-isolating indoors, it’s safe to say a global pandemic doesn’t do wonders for your love life. Thankfully, the summer months have ushered in a wealth of opportunities to reconnect with that special person in your life and enjoy what Toronto still has to offer. There is plenty of fun to be had outside and the province’s stage two reopening plan has helped open many other doors, too. So, with that in mind, here are 12 out-of-the-box date ideas filled with activities to reignite the spark in your relationship.


toronto date ideas
Image: @chosang_tenzin

’50s back in fashion

Saturday nights aren’t cancelled, so why not stroll the streets in ’50s fashion? Find some vintage threads at Black Market on Queen West or Expo Vintage on Dundas and take your date out in retro style. Start by picking up some Cheesey Lucys or a Compressor from Burger Factory in Oakville (don’t forget the funnel cakes) and head to the 5 Drive-In to elevate your Netflix and Chill game. Take the long way home along Lakeshore and find a spot to go for a slow walk at Humber Bay Shores — great for curing the quarantine blues.

Birding is the word

Give the term “love birds” new meaning by spending the day birding. The Leslie Street Spit is a great place to start your birdwatching adventure — more than 300 species of birds exist at this tucked-away spot. Spend an hour or two seeing how many birds you can find (or just enjoy the sunshine on your face). Since you already have your head in the clouds, why not follow up on your avian adventure by sharing some kimchi fries, ceviche shooters and drinks at the Rooftop at the Broadview Hotel (the new Beer Garden and Grill are also worth a stop). After dinner, round out your newfound love for birding at home with the classic comedy The Big Year.


toronto date ideas
The Frank Gehry-designed AGO

The art of the matter

“Art and love are the same thing: It’s the process of seeing yourself in things that are not you.” So says Chuck Klosterman, and that’s why any date that includes a trip to a gallery or museum is often a wonderful experience. The city’s major galleries are opening up. At the Art Gallery of Ontario, non-members can purchase single tickets beginning on July 16. And a visit to this stunning Frank Gehry–designed building is always a pleasure and never too crowded. The exhibit of mesmerizing Diane Arbus photographs is the perfect antidote for the times as is a short side trip to embrace the majesty of the Group of Seven collection. Keep your head in the clouds afterwards and take a walk through the nearby University of Toronto campus. Finish the afternoon by picking up some of the city’s best Italian at Harbord village’s Piano Piano just outside the university gates.


toronto date ideas
Rosalinda’s charred broccoli and coconut soup from the open source cookbook

Farm to your table

As the gorgeous weather reminds us of the 2020 summer that could have been, there are still lots of ways to safely get at the activities that make Toronto summers so memorable. Start your morning with a romantic stroll through the modified Evergreen Brick Works Farmers Market, where you and your partner can still enjoy farm-to-table eats by shopping around for what you’re craving or by pre-ordering an Evergreen To-Go Box ($30–$95) of assorted delights. After taking in some fresh air and supporting local businesses, head home for a romantic night of cooking up your haul and sitting down to a delicious meal together. If you’re stuck for ideas, chef Nick Chen-Yin has compiled an incredible open source cookbook with recipes and tips from dozens of your favourite Toronto restaurants and chefs.


toronto date ideas
Rosé to go at Niagara’s 13th Street Winery

Wine the day away

As of mid-June, wineries were given the green light to start reopening certain aspects of their in-person programming, and there are already plenty of ways to safely explore stunning vineyards and treat yourself to the fruits of their labour. Hidden Bench Winery is serving its wine by the glass on the patio, and you can book a tasting as of June 26. Thirty Bench Wine Makers, 13th Street Winery, Jackson-Triggs, Château des Charmes and Inniskillin began running wine tastings by reservation in late June, most with four-person maximums that will make for the perfect intimate experience. Be savvy with your reservation times, and you and your partner can hit a few of these neighbouring spots to make the most of your romantic getaway. Or, if you’d rather have someone do the planning for you, Grape Escape Wine Tours has extensive safety protocols in place and lots of options for bike and vehicle tours.

Broadway talent direct from your front porch

Got a thing for show tunes? Or just love a good performance? The very talented folks at the Musical Stage Company have something very special worked up. Beginning July 18, the company will offer intimate performances for front yards and driveways across Toronto. Porchside Songs offers three 40-minute concert experiences performed by absolute gems of Canadian theatre including Vanessa Sears and Beau Dixon, Andrew Penner and Hailey Gillis and the Asian Riffing Trio (Colin Asuncion, Chris Tsujiuchi and Kevin Wong). Pick a date, and Musical Stage will take care of the rest. And a night like this demands delicious wine and nibbles, and that means a stop at Paris Paris, which has some unusual and fantastic bottles available for takeout or delivery along with snacks.


toronto date ideas
Sunset on a Tiki Taxi

Temptation island

With the city’s best beaches now opening up on Toronto Island, it’s time to set up a dream adventure in our own sandy paradise. First, book a delightful little ride over to the island via a private service such as the kinda funky Tiki Taxi and make sure to include a short tour of the lagoon and inner channels. Next, head down to the Mahjong Bar bodega and pick up a delish gourmet picnic basket along with a groovy cocktail kit. Make sure to pre-order. After the tour, head to Ward’s Island beach, easily one of the most scenic and least-crowded spots in town — clean water, great views and some secluded spots for a romantic afternoon. Follow it up with a walk along the boardwalk that stretches along the island’s south shore.


toronto date ideas
Geodesic domes at Hotel X

A well of inspiration

As much as you love your partner, spending the last four months two feet away from one another could make even Romeo and Juliet rethink their fevered plans about forever. Reconnect, unwind and address the stress that’s accumulating in your bodies by planning a wellness date night. Start by checking out the schedule of virtual classes at the Chi Junky Yoga Studio and drop in to the Zoom class for just $14, or peruse the big list of live-stream options at Misfit Studio to find one that’s right for you. If you need to get out of the house before you can even think about peace of mind, you can follow social distancing guidelines by working up a substantial sweat in a geodesic dome on the grounds of Hotel X between June 21 and July 31.

Backyard Woodstock

One of the hardest things to take during quarantine is the lack of live music. The energy, the excitement of sharing a concert experience with your partner, and a few thousand buddies, is hard to top. But why not try? Luckily, many great artists are offering up free live-stream concerts and concert videos. So, why not turn your backyard into an outdoor theatre and let the good times roll — all you need is a digital projector for your laptop and a good Bluetooth sound system. Throw a sheet up at the back of the house and tune into Depeche Mode’s Live SpiRiTs concert the band is putting on YouTube. Or check out some local talent on Dan Mangan’s Side Door Access streaming service. A few Toronto artists sharing great streaming concerts on the regular include Ron Hawkins, Sarah Slean and Steven Page. To add some authenticity to the experience, pick up some Houseplant Indica pre-rolls from midtown cannabis retailer The Hunny Pot for you and your loved one to enjoy.


Sporting life

Nothing says budding romance like falling flat on your face while trying a new sport together. With physical distancing a must, the local softball league is pretty much off limits for the foreseeable future. Why not try a new activity together or with a (socially distanced) group of friends? Here are three perfect sports for maintaining distance and having a good time:

In-line skating is back in a massive way, with everyone from kids to seniors hitting the streets on four wheels. Sales of Rollerblades have spiked, and they’re easy enough to find online if you don’t have a pair collecting dust in your closet.

A few videos of slackliners have been making the TikTok and Instagram rounds since quarantine began (only you probably had no idea what those people were doing!). Start by checking out some YouTube videos on how not to fall and tie your rope low enough not to do any permanent damage. There’s no better ice-breaker than attempting to walk a tightrope in the middle of a busy park! Slacklining is just goofy enough and a great exercise.

Disc golf is the sport you’ve probably seen but never tried. Now’s the perfect time to see if throwing a disc at a target is your hidden skill. Toronto has a few disc golf courses, including Toronto Island, the Beach and E.T. Seton. You can buy a disc golf set for around $20.

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