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Tuscany agriturismo: near San Gimignano, Siena or Montalcino?

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We are two couples heading to Tuscany in October. We fly into Rome but head immediately to Orvieto to spend the night, see the town, and pick up a car. We have 5-6 nights to spend in Tuscany and would love to stay at an agriturismo. We'd ideally like to have breakfast included and be within walking distance to a town (this could be 1-2 mi). We'd like to visit hill towns between Montalcino south and San Gimignano north. Not sure about driving distances, so unsure where to stay. Should we stay centrally around Siena? We would like to spend a day there but not stay in the city itself. We could then go north and south from there...but not sure this is necessary if driving between the towns is not far. I found an agriturismo named Guardastelle (sp?) that looks fantastic (walking distance to San Gimignano), but might be too far to drive south to Montalcino, Pienza, Montepulciano. From Tuscan countryside we head to Florence and then to the Cinque Terre (hoping the towns have recovered from the tragic flooding).
Would appreciate any advice or recommendations!

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