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1 month in Tuscany- where to stay

We are traveling with our 1 year old to spend a month in Tuscany in September. We are thinking about 2 weeks at one location and another 2 weeks somewhere else as a base to explore the area. Any recommendations on where we could stay? Thank you.

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Beginning September I'd stay in a cooler place (along the coast or mountain). A place near grosseto would be good (Castiglion della Pescaia?). for later in Sept, One good base for the interior is around Colle Val dElsa, half way between Florence and Siena.