@JonathanB That's so exciting!! Congrats on the upcoming proposal! So it sounds like you'll be here in Toronto in October correct? (based on the CN tower and skydive mention)
I agree with @acw271011 that those are great places but not the most private for a proposal if you're going for that. If you do want a little more public setting than those are big iconic sites in the city for sure.
If you like the CN tower for the view you could book a reservation for dinner at the 360 restaurant (the rotating one that gives you a view of the entire city) or for something similar you could take her to The One Eighty (top of the Manulife centre at bay and floor) which also has AMAZING views and a rooftop balcony that you can have a gorgeous romantic moment.
If you are willing to travel outside of the city - along the lines of Niagara Falls which you mentioned, you may want to consider Niagara on the Lake. It can be a bit pricey that time of year but will be absolutely beautiful in the fall. It's my favourite time to visit. They have some really amazing b&b's, great restaurant and many many wine tours available (if you're into that).
I also love the Distillery District - the cobblestone, the lights, it's very charming...I really love walking around that area.
Is she from Toronto - is there a place that has special significance to her? That would also be very special.
Edited by snswedding2016, 14 August 2015 - 07:00 AM.