Here are some thoughts of a traveller to Italy ..
"It might be worth it to invest in a Lonely Planet book for Italy. It will give you good advice on places to see, some of the history, dining suggestions, a list of cheap hostels, and good maps of city centers. Hostels are nice and cheap and a great way to meet fellow travellers if you are willing to deal with sharing rooms. I would say plan to take the train rather than renting a car. Trenitalia and other train companies are rather cheap if you are just travelling within Italy. If you are going from the north to the south you might even be able to book a overnight sleeper to save on lodging for the night. Trattorias and osterias are supposed to be cheaper eats. Ristorantes are more upscale. Try a risoteria, multiple dishes of risotto, and limoncello. Never eat in a main square/touristy area. Don't expect food there to be much like Italian food here. (i.e. garlic bread, caesar salad, and heavy red sauces do not exist) Rome - obivous places to visit are coloseum, castle st. angelo, st. peter's basilica, pantheon, and trevi fountain (beautiful at night) Venice - I personally thought it wasn't too worth it. Don't plan more than a day here. Pisa - Not too much to see here except for the main plaza where the Tower is. Worth seeing though. If you made it out to here you might want take another day in this area and check out Cinque Terre. It is the considered the Italian Riviera. Seaside cliffs and five beautiful small towns. You can hike from the first town to the last through hills, vineyards, and woody areas. Medium level hike. Or come here to relax towards the end of your trip. Milan - Only thing to see here really is the Duomo. Second most beautiful curch after St. Peter's in Rome. Only other thing to do here is shop for expensive stuff. Don't go on a Sunday though because everything will be closed. Verona - Smaller town between Venice and Milan. It's very quaint and has an amazing opera stadium. If you are into it at all, I say it's worth it to try to catch a performance. During the second act of the opera, when the sun is down, local tradition is to bring small candles and light them up, so you see a stadium full of candle light. Sicily - It's actually a lot of travel time to get to Sicily so you might want to stop by Naples or Messina to make it a little more worth it."
