Elina, since this will be your 1st trip to Italy, spending time in the library, and reading the guidebooks is a great way to get an overview, and to plan your trip.
I believe that is imperative that you read Rick's "Europe thru the back Door", and his Italy guidebook. (Each time when we leave for Europe, I always take copies of guidebooks with me. They are invaluable.)
Another neat thing that you can do is pop over to Edmunds and talk to some of the Rick Steves travel advisors. Once you have done some reading, they could help you to plan a trip.
You may want to consider signing up for one of Rick's escorted tour's. I'm sure that Swan could tell you how relaxed you would feel if you went on an escorted tour your 1st time. On our 1st trip to Italy, we were escorted by friends that had gone to school there, so it was easy. Now we just go by ourselves, and we do not speak any Italian!
OH, getting an auto trans........just go to the autoeurope.com web site and follow the links