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Tuscany -What to see?

We are staying in a small hill town called Montefollonico which is near Pienza and were wondering if we should drive or take the train to Siena and Florence. We would go on two different days. Also, we will be there for a week and were wondering what highlights we should see. We have been to Italy before but not to any of the small towns. We are traveling with a family of five and all older kids and will have a car. I would love to see Assisi, is it worth the ride? Thanks for an input.

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