I grew up learning to drive in NYC, the Brooklyn docks was where I learned cobblestones and truck evasion, and 7th Avenue in the Garment District was where I learned man-pulling-trolley evasion. The rest was learned on Long Island.
In NYC people drive crazy (all the better for learning in) but streets and avenues all pretty much stay the same width and the same number of lanes, and, except for cabs, mostly people stay in the lanes and obey the traffic lights. Lots of horn action but pretty much predictable driving.
I have also driven in Rome. The place, for a Rome driving virgin, is nutso. Cobblestones and potholes, buses everywhere, motorcycles (motorinos) drive wrong way on one way streets, in the wrong lane on two way streets, on the sidewalks, weaving in and out, and traffic lights are pretty decorations for them. Parking is crazy so people don't just double park like in NYC, they park anywhere and everywhere they can notch out enough room for their vehicle. And then there are the pedestrians.
And if you go south, Naples ramps it up another level yet.
Nobody has yet mentioned in this thread all the other things you need to be aware of driving in Italy. If you don't know the acronyms it is worth finding a good guide to driving in Italy, complete with images of the signs you will see or you may have a mailbox full of expensive letters some time after you get home. Be familiar with the way Bus Lanes work, ZTL, TUTOR, IDP, GRA.
I drive often in Italy (not in Rome, Milan or Naples, and Florence just has far too many ZTLs for me) and love it. I took the time to learn the rules and try to drive with my local head on so I am predictable to the other drivers as they are to me. I've never had an issue.