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Stumped over mid-portion of Tuscany trip planning

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Hello,

DH and I, our 1.5 yr old son, and my parents will be spending a couple weeks in Umbria/Tuscany in late May and early June. We are interested in Etruscan ruins and great Medieval and Renaissance art and churches. We enjoy wine but this trip will not be devoted to winery touring although we hope to do at least one tasting somewhere. As we are traveling with a young child, our itinerary is slated to be slow and flexible. We will have 2 rental cars so as to free up my folks to do some sightseeing without toddler in tow.

On the southern end, we're planning to spend 4 nights in Orvieto (works out to 3 days). We booked Casa Selita B&B which has a garden (great for our son), is within a short walking distance from the walls of the city (to accomodate easy returns to the hotel if necessary), and has easy parking and is in a countryside-like setting. We plan to daytrip to Chiusi to see the Etruscan museum there if it is open in June which I can't seem to figure out.
On the northern end, we're planning to spend 3 nights in Volterra at La Primavera, another small B&B that is situated just outside the walls and has an outdoor space for our son to run around a bit. Probably daytrip to San Gimignano.

The middle part of the trip is what has me stumped. We have 3, possibly 4 nights. I've considered Siena (Hotel Santa Caterina) because I know we want to spend at least a day in Siena. But Siena seems to be a bit big and sounds difficult to drive in/out of, even if you do stay just outside the walls. I thought of Cortona since I know it has an Etruscan museum, but read about the crush of Under the Tuscan Sun fans and did not see any accomodations just outside the town such as we have found with our other two locations. By the way, I'm not knocking the book; I liked it. So maybe Cortona would also be better as a daytrip for us to see some of the art and stop in the museum.

So... any suggestions for a base for this middle part of our trip? Our hotel or B&B accomodation range is up to 200E per night although we aren't really aiming for luxury properties (such luxe amenities are rather lost on a 1 year old :-)). It would be very helpful if there was a grocery/daily market in town since most of our lunches will likely be picnic style. And we really like staying just outside the town but within walking distance.

Many thanks for your advice. I'm not usually wishy-washy about planning an itinerary but this middle portion of the trip has had me going back and forth since October!

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