I found a good deal on a flight to Milan for March, just after I will finish a major project at work so I went ahead and booked it. It was $615 RT to Milan, and I had a $500 gift card on Delta so it cost me $115 out of pocket so it was pretty hard to resist. I fly out 3/11, arrive MXP on 3/12 early afternoon and return on 3/22 in the morning. I'm thinking 2 nights at the end in Milan for sure and either 3-4 nights in Florence. For the 3rd location, I'm debating between either Venice or Parma / Bologna. I've never been to any of the cities I'm considering. I'm interested in Parma and Bologna as I was thinking about taking a food tour there, but I'm also interested in Venice as I really like art and architecture.
Rome is off of the list as I will be visiting there in December for 5 nights as part of a trip to both London and Rome with my mom.