Yes, welcome to FlyerTalk and Italy is a fave among many of us here. I'm sure we'll be able to offer an abundance of advice once we know what kind of miles and points you have. Sometimes Rome and Milan are difficult to redeem to in season and I've always had great luck redeeming into Nice. France and then renting a car or catching the train into Northern Italy.
Again, welcome to FlyerTalk and we all look forward to helping you in any way we can.