We travel between the United States and Italy roughly six times a year. Additionally, we talk with our guests all the time about which travel resources they use for their airfare. Based on our own experiences, when scheduling flights to Italy, we generally suggest that our guests take advantage of the larger travel websites to find the best deals. We usually rely on Travelocity ourselves, but have also found some good fares at Economy Travel. On one trip we used Priceline for an emergency 'We have to leave today' trip. While it was disconcerting that you don't know much about your trip until after you have made the purchase, in our one experience, it turned out great. Actually, we wanted to go from Los Angeles (LAX) to Rome (FCO, and our favorite airline for the trip is Lufthansa, but all their flights were either booked or $2,500 each for ECONOMY! We ended up paying something like $400 through Priceline, and wound up on one of the same Lufthansa flights that would have cost thousands.
Here are some links to the travel sites discussed above:
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We strongly urge anyone that is visiting Italy to rent a car, but only for time you spend outside of the major cities. In other words, if you are spending part of your trip staying in Rome, Florence, Naples, Milan, or Venice, use public transportation in those cities. However, the moment you want to venture out into the countryside, wine country, the Tuscan and Umbrian hilltowns, etc., if you are without a car, you will lose a great deal of the experience that awaits you. This is because the Italian train system, while extensive, really focuses on connections between major cities, and many of the smaller and more special destinations in Italy are not connected. Trying to use public transportation in these areas will be a huge waste of time between major train routes, small routes, and busses. If you rent a car, on the other hand, you free yourself to experience the beauty of Italy on your terms.
For those that are afraid to drive in Italy because they have heard how crazy Italian drivers are, don't worry. For one thing, extremely strict enforcement of traffic laws in recent years has served to calm Italians down on the road. More importantly, however, the 'crazy' driving is really limited to the major cities. Once you get into the countryside and the small towns, they calm down significantly.
As for what to rent, the first rule is to rent the smallest thing you can fit into. Most Italian towns were built centuries ago, and they lacked the foresight to plan ahead for Hummers :-). Instead their concept of a large vehicle was an extremely muscular horse. That said, if you get a big car, you may find places you just can't drive.
As for where to rent, we simply suggest Dollar Rent A Car
 . They have multiple locations in Italy, offer Automatic Transmission for those of you that want it, and have generally newer cars than some of the others. Additionally, they are on-site at the airport in Rome and have competitive rates. For cheap short-term car rentals, we generally use Sixti.
Here are some links to the car rental agencies discussed above:
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