20 Nights in Italy!

Many of the Italian cities are not large enough to have well known car rental companies. You might consider looking at AutoEurope.com to see if Assisi has a rental agency. You might do best to pick the car up in Florence or Orvieto where Hertz is across the street from the train station.

I'm glad you've already got your feet on the ground in Tuscany. You know now what to expect out of the trip, and you should have a great time.

Oh I envy so many nights in one country. Your Italian ought to be pretty good by the time you go home.

This trip looks perfect! We have visited those places and I like your pace, not rushing about.
Check AutoEurope’s website for where car May be picked up, dropped off.
Spello- Flower dedecked. Look up all the small alleyways. We spent two weeks there, magical with a plethora of good restaurants. Walk up the village lanes to top area. There is parking at the very top.
Have a coffee and pastry in the garden behind Bar Bonci where the locals go. Such nice owners. I would stay in Spello and day trip to a more crowded Assisi.
Yes to Perugia. Parking garages are lower in the hillside. Escalators up! Lots to see, much history..
Views of Assisi, and from Assisi, of Spello!
Assisi- go up to the Eremo. Visit inside and then walk on the paths through the forest, passing religious sites.
Loved Bologna too, the food especially.
Great itinerary!
We are in Sicily ending a trip the length of yours. We also spent time in Puglia. Retirement gives you the time to do slower travel!

It's easy to get a car while in Assisi. Just take the train a few stops to Perugia. Make sure you get off at the main Perugia station, not Perugia-Ponte S. Giovanni. The rental agencies are right there, at the station. For visiting Perugia, you can take the minimetrò right into the historic center from the train station, or if you're going in another day, there's a huge free parking lot at Pian di Massiano/Piazza Umbria Jazz and a metro stop there. Perugia is fantastic--but then again, I'm prejudiced, living there part of the year.

You'll definitely want to visit Ferrara while you're in Padua (30 minutes by Freccia or 1 hour by regional train, no changes) rather than in Ravenna (over 2 hours, at least one change). That will call for adding one night to Padua.

I've always wanted to see Gubbio but haven't yet managed it. It would be easiest from Assisi while you have a car, though I think it can be done by train (80 to 90 minutes) with a short bus leg. Just one more place to research to see whether it seems that it would be appealing to you.

Edited to add: I should also have mentioned Vicenza, a very nice possibility near Padua. Vicenza is smaller and more laid-back. It's known for Palladian architecture.

Lovely itinerary, except that my personal experience of Padua was very underwhelming. I'd prefer Verona over Padua any day. From Verona it's an easy half-day excursion to Mantua.

Have not seen Vicenza, but I understand it has charm. There's a bit of an inside joke that Rick Steves eliminated Vicenza from the guidebook because there's no place to leave your bags while you explore the town.

Ferrara is a much easier day trip from Bologna. There are more trains and the ride is a lot shorter.

Thank you for all the helpful advice! Spent some time today adjusting our itinerary to include your suggestions for car rental and best bases for day trips. Fortunately I started looking at hotels/apartments--there's an international children's book fair during part of our stay in Bologna, so we needed to make some minor adjustments--easy to do at this early stage of planning. It's great to have input from others' experiences!