I visited Montreal a few years ago. I really really enjoyed it.
The city was a great mix. Big enough to wow a hick like me, but also felt accommodating, friendly, and cosy.
Great leisurely bicycling next to the river and canals.
All the french makes it feel like I'd traveled much further. I also tried making an effort to speak it, and unlike when visiting France, people actually had the good taste (or angelic patience) to indulge me.
It was somewhat expensive, but not obnoxiously so.
I know tourist experience a place differently than residents, but I can totally get it why it's a desirable place.
I did this with my wife for an anniversary. We're most certainly coming back when hitting a nice round number again.