Locally? If I could cheat it a bit, probably Kingston, ON (metro pop. 160,000). Fairly vibrant, historic university city 2 hours drive/train ride from both Toronto and Montreal.
Kingston Ontario at Night by
Jack Tome, on Flickr
Otherwise, one of the other Victorian towns along the Lake Ontario shoreline like Cobourg or Brockville would work.
Globally though? I'll happily live in any Mediterranean or Alpine town. Maybe compromise between the two with somewhere like Lake Como.
https://www.vrbo.com/436662ha