Romantic Rendez-views: Breathtaking Toronto Lookouts for Lovers

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No matter what time of year, Toronto offers scenic backdrops for any romantic occasion. Local writer, Natalie Taylor, uncovers the top spots for romance with a view.

Silhouette of couple on beach in front of Toronto skyline at dusk.
Skyline view from Toronto Islands

There are plenty of opportunities for romance in Toronto beyond Valentine’s Day. This is a roundup of my favourite local destinations, both famous and lesser-known, to take in Toronto’s views and have a romantic moment with a loved one, should you be inspired.

Attractions

Casa Loma

Make your way uptown to Toronto’s only castle for views made for a king and queen. Access to the grounds and estate gardens is included in your admission, which includes the Secret Garden from May to October. The grounds overlook the Annex neighbourhood all the way to the CN Tower, making this one of the top wedding venues in the city. Make your way up the Casa Loma (or also known as the Baldwin Steps), where Spadina Road is split by Davenport Road, for a free yet magnificent vista of Toronto in all of its glory. It’s well worth the hike to the top for couples who like to explore.

The CN Tower

You can’t mention a “lookout” or the iconic views in Toronto without calling out one of the world’s tallest towers at 533 metres. The fast-moving elevator and the glass floor will have you holding onto your date, while the floor-to-ceiling Lookout Window provides an expansive panorama of the city. Or, go another 33 storeys higher to the SkyPod, which is one of the highest observation platforms in the world. At dinner or over drinks, you’ll get a constantly different outlook from the Tower’s 360 Restaurant. Oenophiles will enjoy having a glass of vino from one of Toronto’s highest wine cellars. Adventure seekers can take their love to soaring new heights by doing the EdgeWalk, which allows you to walk around the outer edge of the Tower’s main pod at 116 storeys above the ground. If you muster up the courage to go, aim for a game day when you can see the open dome of the Rogers Centre.

Restaurants & Patios

The Broadview Hotel

What once was tawdry strip club, Jilly’s, has now been transformed into a boutique hotel and opened a previously inaccessible rooftop that now boasts one of Toronto’s best skyline views looking over the River Street bridge. In the winter, warm up on the rooftop patio while you take in the west-side views. A perfect pre-or-post meal activity at the hotel’s newest restaurant, The Civic.

Toula Restaurant

Located on the 38th floor of the Westin Harbour Castle Hotel, you’ll find Toronto’s *other* rotating restaurant, featuring unobstructed views of the Toronto Islands. Post-Italian meal, take a stroll along the revitalized Harbourfront over to Toronto’s Music Garden for people-watching or making your own Secret Garden moments.

Canoe Restaurant

54 floors up the TD Tower, Canoe is known as one of Canada’s best restaurants but even locals forget that if you can’t get a reservation, their bar is the perfect (and less expensive) way to celebrate a special occasion while taking in those sweeping views of Lake Ontario. Nowhere else will you get a selection of some of Canada’s finest wines in addition to a rotating list of seasonal cocktails. You can also bring your own wine for a $45 corkage fee. It’s the perfect “just married” pit stop after a City Hall wedding.

Kōst at Bisha Hotel

Kōst’s balmy interiors are a welcome respite from Toronto’s bone-chilling winters. Floor-to-ceiling windows that showcase Toronto from every angle surround tan and cream furnishings like cozy banquettes that make you feel like you’re in a cabana. Kōst is the new see and be seen spot on Toronto’s radar. 44 floors atop the Bisha Hotel, you’ll feel like you’re next door neighbours with the CN Tower, an impressive view that peers down on a luxurious swimming pool and sleek cabanas during patio season. Hotel guests and residents get swimming privileges but if you’re travelling with a special someone, there will be no greater romantic moment than a sunrise swim underneath the CN Tower.

Lavelle

Slinky pools surround the 360 view including jaw-dropping sights of the CN Tower and of the downtown core. Inside, book the corner booth for that “you feel like you could reach out and touch the Tower” view over their tasting menus (options of 7, 10, or 15 courses) or a shared Mont Blanc. First date? Sit side-by-side 16 storeys above King Street while you splurge on ritzy cocktails. Anniversary date? Time to pop the champagne or enjoy a bottle of Sancerre with each other. Membership grants pool and cabana access, perfect for a post-swim snuggle.

Outdoors

Toronto Islands

The Islands are a Toronto icon and for good reason: their location provides a prime view of Toronto’s skyline. Though summertime is prime time to explore the back beaches and bike from one end of the island to the other (or shed a layer or two at the clothing optional beach at Hanlan’s Point), it’s in the fall and winter, where the crowds dissipate and you’ll feel like you have the Islands to yourself. The barren branches of trees add a dramatic perspective to the choppy and frozen waters of Lake Ontario for a romantic moment set out of a Jane Austen novel. Wander through the streets of Ward’s and Algonquin islands to gaze at the houses and stay a while by renting out a B&B for the weekend.

High Park

Toronto’s largest urban park is full of nooks and crannies for a rendezvous. Take your sweetheart to the lookout at Grenadier Park with views of Lake Ontario on the horizon, ideal for all times of the year. In quieter moments (especially late at night), this is an ideal end to a perfect date. If you can brave the crowds, take a stroll together through the blooming Cherry Blossoms in the spring. Grab a picnic and watch Shakespeare in the summer months. High Park is also a stopping point for an adventurous date. Ride your bike along the Martin Goodman Trail, make a pit stop at Cheese Boutique and bring your foodstuffs to the park amongst the trees for ideal people watching or gazing at each other.

Scarborough Bluffs

The jutting cliffs and surrounding marina on the edge of Bluffers Park make for a dramatic backdrop to an intimate moment. Though popular in the summer months as a beach destination, dreary spring or icy winter days will encourage a warm embrace. If you get a chance to watch crashing waves against the stacked up rocks, it’s even more romantic. Bring the blankets to cozy up!

The Port Lands

Once a gritty wasteland en route to Cherry Beach, the Port Lands is one of the lesser-known spots in the city to grab your partner and a glimpse of the glittering CN Tower and surrounding buildings. Best for a steamy make-out session in the car in frigid temperatures or a scenic bike ride and reward in the summer months. If you don’t want to hang out in the parking lot for the view, head to Cabana Poolbar, cocktail and comrade in hand on a slow night (like a Monday or Tuesday night).

Riverdale Park

Riverdale Park is now known as an Instagram darling for its sweeping skyline views, worthy of the photograph year-round. Break out the Hudson’s Bay blanket and bundle up in the winter on top of the hill. Up the romantic ante with a winter picnic post-toboggan or people-watching while wrapped up in each other. Skate, perch on the hill and then eat or drink after. First dates can thaw at Rooster Coffeehouse, matcha lattes in hand. In the summertime, enjoy free movies and sunset picnics atop of the hill, finish with Vietnamese coffee-flavoured ice cream at Wong’s Ice Cream in nearby East Chinatown. Consider catching the sunrise here before the city wakes up for even more romantic vibes.