I lived in Rome for a semester... right on the Campo de Fiori. Anywhere you go is going to blow your mind. You should see the Forum, Colloseum, St. Peters (The Vatican), Castle St. Angelo, Pantheon (not to be confused with the Parthenon in Athens!), etc. All within walking distance and lots of small sight along the way. Get some gelloto at Giolittis then just walk around or sit and enjoy the sights:

In northern Italy, there are many great small towns but my favorites are: Mantua (check out the Pallazo del Te), Verona (home of the real Romeo and Juliett), Vicenza (lots of Palladio's work), Parma, and like Nick, I loved Assisi, too. (If you eat meat, get some porchetta nearby... it's so good!) Don't worry if you miss any of this stuff... you can't go wrong just wondering Italy and trying new stuff... it's all good.
Screw the net, Surf the backcountry!
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