Any city that can be the butt of a Simpson's joke ("That's it! We're all going back to Winnipeg!") and simultaneously one of the most vibrant cultural centers in Canada is tops in our book. The city's history of isolation and self-sufficiency means that Winnipeggers are unpretentious and sincere (and fun-loving enough to name Homer an honorary citizen). Though the winters are long and cold, there are plenty of indoor activities to both keep you warm and stimulate your imagination.