Italy is often associated with cycle sport and I believe there are some excellent rides over there, but certainly the cities that I've been to (only Rome and Naples) don't look at all encouraging to cycle around.

Naples is almost a perfect example of how to cram in cars into the smallest possible streets and a lot of the streets have to have metal bollards to provide some kind of protection for the pedestrians from the cars and mopeds.

Yes, both Rome and Naples are in the "South" of Italy, and the situation is worse there than in the North.

Milan, Ferrara, Bolzano, Modena, Bologna are just some Northern cities where cycling is encouraged and I can see them trying to get a better infrastructure; but unfortunately there's still a long way to go.