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Apartment or B&B in Tuscany town - doing it differently this time - help!

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In October, we will be traveling to Italy for the 4th time in the past several years. In addition to Rome, Venice, Florence, and Cinque Terre, we have traveled some in Tuscany and Umbria, mostly staying in Agriturismos (in the Chianti area, Val d'Orcia, and outside of Orvieto), as well as one week in the tiny village of Montone. This time we would like to stay in an apartment or B&B WITHIN a town or larger village in southern Tuscany (or maybe Sienna?) - something large enough to have at least several restaurants to enjoy in the evenings after touring in a car, and a place to slow down and explore. Are there any suggestions? I have briefly visited most of these during the day, but want to enjoy our spot in the evenings when fewer tourists are around. I have considered Montalcino, Montepulciano, San Quirico d'Orcia, Pienza, and Siena. We have stayed before in Monticchiello for 2 nights, and it is too small for what we are looking for in a one week stay. We are interested in good food and wine, maybe visiting a couple of markets, and in general exploring the area. Also, are there any recommendations on any apartments, B&Bs, or hotels in any of these locations that would make a stay there special? An apartment would give us an option for local shopping and cooking, but we would take a hotel in town vs an agriturismo in the countryside. We would appreciate any suggestions!

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