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Driving Itinerary in Tuscany

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We will be staying at an agriturismo near Vaggio in Tuscany for 7 nights in early October.
Have never been to Tuscany outside of a 5 day trip to Florence.

Would like to ask for help with daily itineraries built around lunch in the following places – San Gimignano, Pienza, Montalcino, Monticchiello, and San Quirico.

In addition to visiting for lunch and exploring, we would also like to include Pienza, Siena, and a tour of Val d’Orcia (thanks to Stu Dudley and others).

Would like to be back by 7:00 as I have trouble driving at night and would also like to have some relaxing time inbetween.

Need help in planning the days from the experts.

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