Montepulciano or Orvieto for a few nights

I haven't been to Montepulciano, but I think Orvieto would be hard to beat for the things you mention. It seems to be a popular destination for Italians, which may explain why there are a lot of solid restaurant options. I especially liked the Sicilian restaurant (focusing on seafood), Cibus.

The cathedral is special, and there are at least two worthwhile museums, the cathedral museum and the archaeological museum. The tourist office has some walking tours.

Orvieto is much easier to explore. Once you are at the top, it's not hilly like Montepulciano. There's more to see and do in Orvieto. It's a thriving, busy, smallish city. Montepulciano is a country, hilltop town. I visited Orvieto long before I visited Montepulciano.

Having been to both towns and based on your criteria, I'd give a slight edge to Orvieto. The cathedral is quite beautiful and there are multiple Etruscan sights. Both towns have great views, nice people and good food, but Orvieto seems to have more good dining options. While I've enjoyed staying in both towns, I think Orvieto has a bit more to offer.

I visited Montepulciano as a daytrip but I return to Orvieto every year for a couple of nights.

If you get away from the area between Piazza del Duomo and Piazza Della Reppublica, you will see narrow streets that go downhill to the medieval quarter. Not too steep, but not flat. There is s little bus that makes a circuit around the town (beginning at piazza Cahen, the funivia stop), in addition to the one that goes straight to the Duomo. If you can take the longer route, you'll have a nice orientation to the city and still end up at the duomo.

The funivia ticket is good for the bus connection to the town.

Be sure to visit the church of San Giovenale, at the opposite end of town. For lodging, my favorite is Hotel Virgilio, but there are lots to choose from.

I have been to Orvieto before, I think it is some of the craftsman shops there that intrigued me the most. Incredible woodworkers. So it will be fun. Staying at Hotel Duomo which seemed reasonable and central. Thanks for the suggestions folks Now..can I escape the ZTL if I have reservations inside ...lol