Went Out with Ipswich to Inter in 2000 uefa cup, obviously do the Duomo etc in the main square and if your eating go for the traditional family resturants off the main square, really friendly and great food at a reasonable price. Best thing we did was grab a train and go upto Lake Garda for the day and do a boat trip really nice (although bloody cold in december). Cracking place kids always on at me to take them back and do a game at the san siro with them. (which is immense by the way). If you fancy some shopping there's a couple of factory outlets if i remember rightly around the city (probably just need to check out online before you go).
Be careful what you dream of it may come up and surprise you.