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Base in Chianti or North/West Tuscany

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HI. We are looking for a town/village to make our base in either Chianti or North/West Tuscany. There are going to be 5 of us (multi generational). We are planning for later part of June 2013. We will have a car, however, our goal is to be in a town/village that that has a few restaurants and shops. I've looked all over the internet, but I am getting extremely confused. We do want to make a side trip up to Peidmont, where my father is from - so maybe somewhere inbetween Turin and Rome (where we will be flying in to). Any recommendations on apartments would be appreciated too.

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