This is our 5th trip to Italy including many of the hill towns. We have never been to Montepulciano before, so hence the question.

For groceries I would look in Chinchiano Terme for a market---the town just prior on S-168. It is flat and will be easier to access and shop.

Bob - excellent idea. Giorgio at Terre di Nano just recommended the same thing. He says there is a good sized COOP there, so will pick up a few things on our way to Terre di Nano.