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Tuscany with 13 and 19 year old girls

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Trying to figure out where to stay in central or southern tuscany . Daughters into shopping , eating , people watching . Parents into food , wine , scenery . My husband does not want to rent a car but would prefer private drivers and or private/small group tours to get around . We all like resort activities as well . Ideally I want to see montalcino and montepulciano . Maybe pienza , san gimignano .

Should we stay in siena and take day trips from there ? Somewhere in val d'orcia?

What about the agritourism experience ?

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