@Hibernate – Sorry, gotta say – the city is actually called Udine. I have some friends who live there, and it’s very much a student town as the university has a few exchange programs.
Florence is amazing and blew my mind.
Rome is breathtaking – there’s history around every corner.
Venice is also pretty remarkable – there’s the whole fact that the city is a series of islands to admire, plus the nearby Murano where they have gorgeous glass.
My first choice would be Florence, because there’s just so much there (and I’m a sucker for Renaissance art/literature), but it is a little touristy in the sightseeing areas.
So I’d choose either Siena (a medieval town in Tuscany) or Orvieto, a town in Umbria. Both are very cobblestone-y and oh-so-Italian feeling.
Assisi is also pretty amazing in that it makes you feel like you’ve stepped back in time, and there’s the Basilica di San Francesco with some pretty superb frescoes.
Okay, so I’d go anywhere in Italy. Except Napoli – I didn’t like it there. It felt too much like Toronto, and so too much like home.