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Please help me with a loose Tuscany itinerary (long, sorry)

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We will be in Tuscany for 7 nights of our March-May trip and I'm having a really hard time figuring out what we want to do. It will be myself, husband, boys ages 5.5, 3.5, daughter 1.5... we are staying at an agriturismo about 2 km outside of Pienza from April 5-12. Essentially this is what I have so far:

April 5: drive from Rome to Pienza, spend that half day in the town of Pienza (i think) and acclimating to our new place
6: fill in the blanks...
7:
8:
9:
10:
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12: leave in the morning, driving to Malpensa to arrive by 8pm, stopping somewhere either on the coast or in Parma (thank you, people who commented on my other thread)

Based on our reading, one or both of us is at least somewhat interested in Siena, San Gimignano, Florence, Pisa, Lucca, Chiusi, Volterra, Montepulciano (I think our farm stay includes a wine tasting here), Montalcino. Perugia was mentioned to me as something my boys might enjoy b/c there is a chocolate factory there, but I don't know if there's anything else that would entice us there over another place. Cortona is permanently etched in my mind thanks to the magic of Hollywood, but I don't know if it's something we want to actually devote a day to. Of all these places, the only one we have visited before is Florence.

As far as what we are interested in seeing, we have pretty much written off museums on this trip b/c of the kids. Short attention spans, and I don't want to ruin someone else's experience by having to hear "when are we going to leave here?" over and over again. We would love to see shorter walk-throughs such as churches and duomos, and we love architecture. DH is a war history buff. My boys will be very excited to climb to the top of anything that will give them a great view. We'll probably be doing a lot of just hanging out, letting the kids run, eating, walking and exploring. Hiking is good, parks are good, animals are good. We're also interested in seeing anywhere "off the beaten path" (I know this is difficult in Tuscany, but what I mean is any less touristy, more overlooked places).

I thought that we would want to plan on one town a day. However, a friend of mine took this same trip a few years ago with her kids who were almost the same ages. She said they did Lucca/Pisa in the same day, and San Gimignano/Volterra in the same day. I don't know if that's reasonable or not.

We will not be married to our itinerary because of, well, small children. We may end up having to drop a destination or two from our "final" plan. What I'm hoping for is some concrete advice to help me prioritize our destinations. If you are reading this and you have any advice on places to drop, add, or anything else, I am totally open! Fire away. Gently. :)

I really appreciate the advice I have received on these forums and I am grateful to those of you who take your time to help others.

cheers,
ET

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