I think this itinerary needs serious work to be enjoyable. As a first time traveller to Italy, I think you could target better locations. I typically look to whack off the further afield place on my itinerary and circle in from there. In this case, I'd get Piedmont out of your plan. Is there a loop trip you could piece together from Milan as your start and end point?
As others have recommended, I'd get out of Milan - ride the train to a near-ish location (within an hour or two) - Use the DB website (German rail) to easily navigate from Milan - otherwise, Rome2Rio is another helpful tool for your planning.
Get perked up with good Italian coffee for your train trip. Set your alarm in case you fall asleep on the train. Read your guidebook. Listen to Rick's audio guides. Do what you can to occupy yourself for the trip and really try to stay up as long as you possibly can to avoid jet lag. Get to your location. Shower off the day. Change your shoes. Go eat and drink, wander off your pasta with a walk about town. Don't get to bed until 10 or 11pm. Next day, rinse and repeat, or something like that.
Parma is an hour and some from Milan. Genoa is like 2 hours from Milan. Do you want Central Italy or water? Eat your heart out in Parma or be a tad cooler in the waterside breeze of Genoa? Move to CT the following day.
You've not shared what you are really interested in. Why Piedmont? Why Parma? I can assure you, food and wine is abundant and you will get your fill no matter where you go in Italy. Personally, Piedmont (Asti and Alba are just ok).
I'd likely go something like this:
Milan (get out ASAP), Parma (1 or 2), CT (2 or 3), Florence (3-4, you may want to hit Pisa, Lucca, or Siena), you could add Venice here (2-3 hours by train from Florence), make your way to Milan from Venice (you could stop in Padova (Padua), Vincenza for a night in between or just move from Venice to Milan). Book a late Last Supper visit. Have your last supper. Leave the next day. Return often and promise to always look for an open jaw flight - flying into one location and out of another. Rookie mistake.
Whatever you do, you and your forty-year-old selves will have an amazing time!