We'll be traveling from Venice and plan to stay for 3 nights in either Val d'Orcia or Umbria the last week of November. My issue is at that time of year, its gets dark early and while we will have a car, we'd want to base in town with restaurants and wine bar as opposed to Agriturismo. We'll explore the area during the day, but want to return around 4-5 pm. rest for a bit then be able to walk to nearby by restaurants, concert, perhaps Christmas market.
We know for sure we want to visit vineyards, working farm (cheese making would be great) and definitely want to explore Pienza, San Quirco, Bagno Vignoni, Montepulciano and the make the loop Rick recommends. We also want to spend one day exploring Assisi/ nearby hill town. We plan to stop in Orvieto after leaving the area on our way down to Rome, for our next leg. We'll be leaving car at FCO and taking taxi/private transfer to accommodations there.
I am stuck on where to best base out of. I like Pienza but the available offerings at that time of year within the center are few and far between. Montepulciano seems to be a good fit, but I am really looking for upscale accommodations within historic center - all I see are smaller B7B or inns - albeit they seems lovely, but really hard to tell online. I wanted to know if anyone has first had first hand experience with Il Tosco, Locandra di San Francesco, or Meuble il Riccio in Montepulciano. San Quirco and Bagno Vignoni look lovely but not sure at that time of the year what might be available to go to each night. IF anyone has been to the area at the this time would to hear opinions. Thanks!