Assisi

Orvieto --- visited already? If not, then Orvieto for sure

Perugia --- Abbazia di San Pietro (Deruta tiles & floor tiles, votives, interesting details), Museo Archeologico Nazionale (+views, courtyard), Galleria Nazionale, Collegio del Cambio (Renaissance art, woodworking. frescoes), Collegio della Mercanzia (incredible inlaid wood ceiling, walls, etc.), Museo dell'Opera del Duomo (Signorelli altarpiece), Tempio di San Michele Arcangelo (very cool)

Assisi --- San Rufino's excellent facade with animals, weird people, etc.

Spello --- Villa dei Mosaici (nice floor mosaics), Church of S. Maria Maggiore (Cappella Baglioni's Pinturicchio frescoes),

Deruta --- ceramics

Gubbio --- 2nd largest ancient Roman theatre (largest = Marcellus in Rome), Chiesa di San Francesco (frescoes + cloister), Museo Civico e Pinacoteca/Palazzo dei Consoli (views + medieval rooms), good restaurants, views and cool streets, birdcage lift to the top of the hill (they will stop it for you if you are chicken to enter the cage while it's moving!)

Citta di Castello --- Pinocoteca (weird Saint Sebastian by Signorelli), 14th century town hall, cathedral

Spoleto --- Duomo (Santa Maria Assunta facade + apse + Museo Diocesano), 13th century aqueduct with nice walks, Basilica di San Pietro (its very very very cool facade is one of my favorites in Italy, just outside of the town across a busy road https://www.viaggiareinumbria.com/altorilievi-facciata-basilica-san-pietro-spoleto/)

Norcia & Castelluccio --- wrecked by earthquake and in process of being restored, both very interesting to visit, good food

Perugia, Spoleto, Gubbio, Norcia, and Orvieto are where we stayed for several nights each. Also Narni. If I were you, I'd stay in a larger, less heavily touristed (and tourist-oriented) place with more to do and better food than Assisi, i.e. Perugia. But others here love Assisi and you have been there before, so you know what it's like.

Sounds like a wonderful trip. Gubbio and Spello are beautiful towns. A less trafficked but impressive hilltop town is Trevi, which is in the same area. If you like caves and stalactites, you could go to the Grotto di Frasassi. Large caverns with graceful formations. Some people like the town of Monte Falco; I wasn't as impressed with it compared to the others mentioned.

Thank you to both nancy and sally. You have given me wonderful suggestions and now I think that 6 nights in Assisi and its surroundings is probably not enough!

Whoops, I meant to say Salty!

landing in Milan and driving to Assisi for a 6 night stay.

Arriving from where? Driving on arrival day? A 6 hr 300+ mile drive may not be a good idea depending on where it is you are flying from.

If an overnight flight from the Western Hemisphere, all you other plans could become moot.

Be safe, have fun.

We are flying from Atlanta to Milan with a short layover in Istanbul arriving Milan at 14:10 and spending one night in there. Departing Milan the next morning for the 5 hr. 45 min. drive to Assisi. It's not a difficult drive. We've done this before and spending the night in the arrival city makes all the difference.