Just got back from Rome yesterday. I do a lot of business in Italy; mostly in Milan.
The food in the south is much better. They don't mess around, 3 course meals for lunch are common. If you want to go to Italy you have to go to Sicily. The weather and scenery is incredible and the food is the best i've had anywhere.
Rome is great because there is a lot to see. The coliseum and assorted ruins are cool and The Vatican is impressive.
Milan is much more of a Metropolitan city, with great public transport (good subway system). There are a number of historical buildings near the center such as Duomo. If you like skiing the Alps are only about 100 km away, which you can see from the city on a good day.