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Need suggestions for our week in Panzano

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I'm sharing a villa in Panzano with a group of friends active 60 year olds. Some of us have visited Tuscany before and for others it's a first visit.
I want to share some of my favorite experiences and try some new things. So far we are planning day trips to Siena, Orvieto, Southern Tuscany including ( Montalcino, Pienza, St Antimo can we fit in Bagno Vignoni?) and maybe Cortona. That would fill 4 days. I would love some suggestions of activitiesor places to visit closer to Panzano.

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