I am planning a 3-week trip to Italy for November 2022. We will spend the first week in Rome. That leaves me with 12 nights that I would like to spend in Tuscany and/or Umbria. I am thinking I would like to divide this into three 4-night stays, though I am open to other suggestions. We will not have a car.
My ideal base is a small/medium town large enough to have plenty of restaurant choices and good walking. It doesn't have to have blockbuster sites, but one or two churches, historical sites, museums, or Roman ruins would be nice. We don't care about night life, and my husband isn't into art. From each base, we would like to take one or two daytrips by bus or train to other towns/sites. It would be wonderful if we could take a 2-5 hour walk into the countryside and enjoy nature. Hills are not a problem. We try to avoid narrow roads with no shoulder or sidewalk.
Assisi seems to check all the boxes. Sienna also looks great, although I don't know if it has any nature walks nearby. I'm now at the point where all the towns that Rick and other guidebooks highlight sound the same to me. (I'm even starting to wonder if I'll get bored with this many days in Tuscany and Umbria.) I would love any suggestions anyone has on good bases in these regions. Thanks!