The holidays can be one of the most romantic times of the year, between cozy outdoor fires and glowing seasonal events. And if you’re ready to take your love to the next level, these incredible destinations may inspire you to pop the question. We’re coming in hot with the best places to propose in Toronto that are guaranteed to impress your future fiancée.

From stunning rooftop bars to a historic castle, here are 8 amazing proposal destinations that you can book in Toronto.

Writer’s Room

This stunning rooftop bar not only has a history of literary legends who shared moments in the space, but the Writer’s Room Bar also offers a beautiful view of the city that will make anyone swoon.

If you want a picture perfect moment that has your city in the backdrop, this is it.

Book it here

The CN Tower EdgeWalk

Declare your love from the top of the city! The CN Tower EdgeWalk will help you celebrate your special moment as you take your relationship to new heights.

If asking for your lover’s hand in marriage isn’t nerve-wracking enough, try doing it from the world’s highest full-circle hands-free walk!

And if you’re not up for the adrenaline, you can also plan a lovely indoor proposal at the CN Tower that’s equally as romantic.

Book it here

Related Posts:
10 of the most romantic getaways for the holiday season in Ontario
11 fun & romantic date ideas to try in Toronto this holiday season


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On a TTC streetcar

This is perfect for the hopelessly romantic Toronto locals — with a big budget. You can charter a TTC streetcar for the ultimate proposal that will blow your future fiancee away.

If you’d like to gather friends and family around, the streetcar has seating room for 70 people. You may want to ask them to pitch in on the cost too because the three-hour minimum price is $2,410.29.

Book it here

Under the sea at Ripley’s Aquarium

The team at Ripley’s Aquarium is happy to help you plan a unique experience for your proposal. You can even recruit a scuba diver to deliver your special message underwater.

But, be warned — a stingray may or may not photobomb your proposal photo. That’s exactly what happened to this Toronto couple back in 2016.

Book it here

Distillery District

A romantic proposal among holiday lights and a massive tree? The Distillery District’s Winter Village has been recognized globally, and is not only festive but totally cute and romantic!

Between carollers, and Santa himself, this would be a magical holiday proposal!

Book it here

Casa Loma

What’s more fitting for a fairytale romance than a marriage proposal at Toronto’s historic castle?

Many proposals have taken place at this beautiful destination, and for good reason. This might just be the most romantic place in the city. There is certainly no shortage of photo ops, especially during the winter.

You can even have your wedding here, just like the former Toronto Raptor Patrick Patterson did back in 2019.

Book it here


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The Art Gallery of Ontario

For art lovers, this is the ultimate proposal destination. If the idea alone isn’t enough to convince you, take a look at this romantic proposal that took place at the AGO back in 2020.

Whether you want to book a private space in the gallery to include friends and family or share your special moment with the Group of Seven as your witnesses, you have plenty of options.

Book it here

An ice skating rink

You can pop the question on ice by renting out an entire skating rink. You can share the moment with your loved ones, or skate around the rink hand in hand while you work up the courage.

Whatever you do, don’t lose your balance and fall over. Unless your partner is ready to catch you, of course.

Book it here

Now that you are equipped with the best places to propose in Toronto, it’s time to start scheming. Good luck!