The winter is definitely the off season in Tuscany. The streets in the small towns often have few people, except on weekends and holidays. Many of the restaurants and stores in Montepulciano are closed. The temperature has generally been in the 40s and 50s, and there may be light rain once per week or so. As we have arranged for a car, we go to short trips in nearby towns. We went to Pienza on the Val d’Orcia side of Montepulciano for lunch and had a walk through the town. It is a very small town that has an impressive church and a palace built by Pope Pio II. Pienza was his home town, but before he could really complete his plans he died. Pienza is now a center for flavorful pecorino cheese. If visiting as a tourist, a morning or afternoon stroll through the town, plus a meal, will be adequate to cover the town. For us the highlight is on the top of the south wall and looking across the Tuscan valley. Many may recognize it from books and websites about Tuscany.
On another weekend, we made a trip to Chiusi. It was originally an Etruscan hill town, later shared with the Romans and eventually became a Roman town. There are several churches with interesting art, beautiful windows, and a nice square.
The cathedral has a nice museum including beautiful music manuscripts, and there is a tour of the Etruscan water underground water system that was used the town at one time.