Montreal, je t'aime!
My personal favourite North American City! It's one of the cities where you can find more or less everything in close proximity, although taking the metro makes it a lot easier. It's very lively and young, full of students. The Old Port area and the Plateau/Miles End have a lot of Quebecois charme and the Downtown area is good for shopping. For going out either the Old Port area or the Rue Crescent off St Catherine Street are perfect. Also, check out the museums, they're great!
Insider Tip:Check out the Parc de la Fontaine in the Plateau Area. Also the all the cafés and little shops around Avenue du Mont Royal and Rue St Dennis are worth checking out. For a perfect refreshing in Winter or Summer, go to Leo le Glacier an Italian Ice Cream cafe at Avenue Duluth close to Parc de la Fontaine