I vote for Toronto - I've never owned a car and I've lived there for 30 years. For a period of time I was car-free, bike-free, and transit-free, I just walked everywhere for about 4 months. I ate, played, had fun, and never missed metal-dependent transportation.

I currently live in Calgary car-lite; we borrow a car for some shopping trips and inter-city travel, but I am able to get to work and do daily chores without a car (don't think I could get by very well without transit or cycling though, it is very suburbanised here).

Considering less than half of montrealers own cars, I would guess that it is a good city to be car free . Anyone care to corroborate??