Decide into which city you will fly to begin your tour of Italy. That decision might be somewhat dependent on your airline. For example, if you fly American Airlines you can land in Rome or Milan. If you choose Milan as a starting point you will have the option of working your way south as you travel.
Make a list of the top ten sites, cities and/or attractions you absolutely want to see in Italy. Start by checking out a few guidebooks from the library and browsing through them; many of these contain their own "not-to-be-missed" attractions that you might consider. Such attractions as the Roman Colosseum, the leaning tower of Pisa, the Ufizzi Gallery in Florence, and a walk in Venice will make almost anyone's list, but by doing a little research, you will easily come up with your own personal list.
Check out information for train travel online before your trip. Traveling between cities in Italy by train is simple, fairly inexpensive, and a great way to relax between hectic days of sightseeing. Planning is simple; for example, on the Trenitalia site (www.trenitaliaplus.com/trenitalia.html), you can plan your route and buy your tickets before you leave home. It's easy to purchase tickets at the station, either at the ticket window or from a vending machine. As soon as you arrive in one city, consider buying your ticket for the next leg of your journey; you're already at the station, and that way you'll have the security of knowing your tickets are in hand. Before you board the train, make sure you validate your ticket by inserting it into the validation box near the tracks; this will stamp your ticket with the date and time, which you must do to avoid fines.
Combine your train travel with driving if you are headed for destinations you can't reach by train. You might check into the various train/automobile combinations that are available. If you plan to rent a car, you will need an international driver's license; insurance is mandatory but is almost always included in the price of the car rental. Check the site in Resources for a sample car rental company. Expect to pay tolls as you drive; you can pay these with a credit card.
Consider using tour guides to help you make your way through some specific sites on your trip. For example, the Roman Forum takes on much more meaning when a knowledgeable guide leads you through it.