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9 nights in Tuscany/Umbria—opinions on itinerary?

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We're going to be in the Tuscany/Umbria region for nine nights around the end of August/start of September. We are traveling with two very young children (3 and 6mo). We've been to Florence in the past, but have seen little else of the region.

Leaving from Rome, we were thinking about
--heading to Siena for 3 nights,
--then to an agriturismo near Montepulciano/Pienza for 4 nights,
--and to a third location for 2 more nights
--before taking a train south to Salerno (for a ferry to Positano). Rome and Positano are set, but the other dates are still flexible.

Is this a good plan? Would you suggest a shorter stay/longer stay anywhere?
I'm pretty set on going to the agriturismo we found, but we could go there first or second. Would Orvieto be too similar to be the third spot?
Should we consider swapping in someplace like Perugia for Siena? Or otherwise trying to base ourselves further east for a portion? (to visit Spoleto, Assisi, etc.?)

A few other details about us:
Other than the agriturismo, I envisioned basing ourselves in a village or city where one of us can walk out during kids' naps or go to a bakery in the morning. We don't want to spend a ton of time in the car with them. We're not totally scared off by steep climbs.
But because of their ages, art museums are less of a priority than pedestrian-friendly areas. Main interests: people-watching, food & wine sampling, photography.

Any help/feedback is much appreciated!

Ashley
http://www.hitherandthither.net

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