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Itinerary check - central/eastern/southern Italy

I planned a fall trip to Italy and in the spring, my husband decided to switch it to Spain. So I planned a whole trip (to Andalucia (thanks in part to several people on the Spain forum here!) and then this past weekend, he decided to switch back. Good thing I enjoy trip planning, lol. So the good thing is I had my original outline to work from, but the bad news is I've spent almost every waking moment the last few days finalizing the itinerary and finding lodging, renting a car, changing flights, etc.

Anyway, would appreciate any feedback on this. I basically have a list of things that interest us that we can do in all these areas (except the last stop) but am trying not to schedule anything so that we can pick and choose what we feel like doing and when. If you have any "can't miss" things you've done in these areas (especially beyond the well known stuff), please post! Thanks in advance!

Arrive in Milan 9/21, train to Parma. Stay in Parma 4 nights. Plan on going to Modena and Bologna via train to explore.

Pick up rental car and drive to Spello (Umbria) for 4 nights. Will go to Assisi and hit some wineries in Bevagna and Montefalco.

Drive to Colascio (Abruzzo), stay 2 nights. Do some hiking.

Drive to Monopoli, stay 3 nights. Enjoy the town and visit a few of the Valle d'Itria villages.

Drive to Matera, stay 1 night.

Drive to Naples, stay 2 nights. This wasn't on our original schedule but it seemed easiest to fly back home from here vs head back to Milan. So have not done any research on Naples. I think we'll just walk around different areas, eat some pizza. No day trips or anything. We will have pretty much two full days and nights though, so if there are any must sees right in the city, please share.

Fly home 10/7