For your first trip to Europe and Italy, I'd suggest picking up the Rick Steves' books and trying his suggestions. I had a hard time with Italy. While I have traveled around a lot in Northern Europe and lived in both Norway and the U.K, the way things are in Italy are different.
Rick's company also produces a free smart phone app called "Audio Europe" that has really good museum and old town walking tours. There's no charge for it too.