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1 week Tuscany in November

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Hi, I am looking for recommendations on which area to stay in Tuscany during a 1 week visit in November (2 adults and a toddler). We will have a hire car which we will pick up from Venice, and return somewhere (?) before going to Rome.
Our main interests are visiting historic villages and countryside (including San Gimignano, Monterrigioni, Montepulciano, Volterra), as well as Siena and possibly Florence.
We wish to stay at an Agriturismo in a self catering apartment.

So the areas I am thinking are Chianti or Val d'Orcia, or somewhere near Siena. What are these areas like in November?
Any advice or suggestions much appreciated.

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