If I may, I’ll add a couple more places to the discussion. Just a bit farther south is Spoleto, a small hilltop city of less than 40,000, but with an infrastructure that includes an easy parking garage below the town, and a combination of moving walkways, escalators, and elevators to help navigate into the city above. There are still some stone stairs to deal with, too, but it’s extremely evocative and scenic. We had a car, and visited towns north of Spoleto, including Assisi, but that’s as far north as we made daytrips from where we were staying in Umbria.
One of those towns, not yet mentioned, was Bevagna, a delightful place. One of the remarkable sights in Bevagna was what used to be the Amphitheater in ancient Roman times, which was converted to housing (“condos?”) in the Middle Ages, which still remain. It’s the one place in the area that’s actually flat, and not a hilltown.
Although where we stayed is addressed “Spoleto,” we actually stayed at an agriturismo about 5 miles west of the city, at Santa Caterina https://agrisantacaterina.it/ . It was October when we stayed, and was clearly not high season for the area - no crowds. It rained heavily one day, but was pleasant the rest.
We visited “downtown” Spoleto as a daytrip, as well as neighboring hill towns by car, and while we could’ve theoretically gone to a town for dinner, we were up some twisty farm roads (almost all were paved) and it was just far enough and dark enough that we decided to not try that at night. instead, we ate breakfast and dinner each morning and night at the agriturismo.
Maria’s an excellent cook, and also runs a shop onsite that sells some of her preserved foods. Her dining room is a potential restaurant, and while we were the only ones having dinner most nights (sometimes her husband, too), a couple of nights there were other people who weren’t staying there.