We will be arriving in Bologna and then staying in the countryside, then returning the car to Milan. Please no driving advice. What I would like are some good recommendations for rental companies from people who have actually done this.
We rented from Hertz last May and bring a damn good GPS.
Sounds like you had adventures. (:-)
Go to www.autoeurope.com and rent through them.
They are a consolidator based in Maine (but present also in Italy) and they will get you a better deal rather than going directly through the rental company. The major rental companies operating in Italy are the well known European and American multinationals, such as: Avis-Budget, Europcar, Hertz, Maggiore, Sixt. When renting a car in Italy, you cannot waive insurance. I also recommend you purchase the no deductible package, because the minimum scratch will result in hefty charges just for the deductible (up to 1,000 euro). Your US insurance won't cover you there and most credit cards won't cover you either in Italy. Watch out for the practice of charging you (after you are back in the US) for fuel even if you return it full. Keep a receipt from the gas station and get documentation from the agency that your tank is full when you return the car. If you rent through Autoeurope, they will help you sort out any dispute when you return. I've rented cars in Italy nearly every year in the past 25 years, and I have to dispute something nearly each time. I now consider disputing with rental car companies in Italy part of the Italian vacation experience, like having limoncello after dinner. It comes with the program.
Do not confuse autoeurope.com with autoeuropa.com. The first is good. The second is terrible (based on lots of reviews).
Thanks Roberto for the info. Thanks Michael for the clarification.