Suitable HILLTOP TOWNS for someone with minor walking challenges... Spoleto, Todi, Montefiascone??

Since you mention Spoleto in Umbria, take a look at Bevagna nearby, It is flat, totally flat and charming. When we were in Umbria we kept looking for flat places for a friend with mobility issues who wanted to travel there. It has everything similar to a hill town without the hill.

Orvieto? Perhaps a bit larger than you were hoping for, but also absolutely charming. Step off the train and take the funicular up the hill. Then take the small bus to the piazza in the center of town... so, no climbing up! Several hotels and B&Bs within a block or two of the central piazza. The streets have some up and down in the center of town, but generally it's a gradual incline. Also some gorgeous views off the ramparts in various spots.

Orvieto also has a bus route through the center of the city that will get you past the steeper incline/decline areas.

Todi's main center is pretty flat but lots of stairs up to the Duomo entrance. There is a local minibus that makes a circuit of the town.

Gubbio is flat around the parking areas, Piazza dei 40 Martiri, and the Roman ruins. The long streets in the old town are relatively gentle switch-backs up the hill while the more direct routes are pretty much staircases. But there are three public elevators/lifts/ascensori that you can take up and down those routes, instead. See the map at http://www.mappery.com/map-of/Gubbio-Map or pick up a copy at the Tourist Information Office (which closes for lunch as do museums and businesses, but not churches).

Here's another vote for Orvieto. Charming, charming, charming. The upper town is remarkably level, and there are incredible views from the town's walls.

Orvieto! I haven't been to all of the towns you mentioned. I did like Spoleto but I prefer Orvieto and have gone back several times. As mentioned not hilly like some of the other towns that I have been in. Beautiful views!

Pienza is flat, a beautiful old town and a pleasant newer part, the nicest amateur football (soccer) field surface I have ever seen not far from the old town walls. Absolutely gorgeous view of the countryside from the rampart.

If you are more interested in Umbria, Bevagna is flat and in the valley but nice nonetheless, and Orvieto is fairly flat once you reach the old, upper part - very nice. You may be able to hire a cart to get across the bridge in Civita, worth it for me but not everyone's cup of tea. Spello and Todi are splendid but very steep.

Todi also has a funicular from the main visitor parking lot to the top of the hill. Once there, the areas at the top are not totally flat but much more manageable. I spent a week in Todi last year, living at the bottom and hoofing it up and down several times per day. It's steep. If you choose Todi, be sure your lodging is near the top. But it is a great town.

Must say again that apart from the main street in Orvieto it can be slightly steep.

Not Montepulciano for sure. Pienza is fairly flat. Orvieto is flat in the center near the Cathedral and there is an escalator up from the parking area. Civita is a nothingburger. It is enchanting at a distance but there is almost nothing there. An hour's visit is way plenty. Lucca would be good although not so much a hill top -- but charming with a town wall still intact.

I would strongly consider Orvieto - it's up on a plateau and not as hilly as other towns. It's been a while, but I remember being able to park near the fort at the top of Montalcino, so you could enjoy wine tasting and crostini (appetizers) at the fort without climbing a hill. Assisi is another one you can park at the top of, and I'll bet it is more accessible than other hill towns due to its religious significance to many.