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Tuscany itinerary - Please help !

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My son plans to visit Tuscany at the beginning of May, with his wife and 5 months infant. They will stay in Florence , visit it and then will rent a car to travel to South (till Rome- at airport).

After leaving Florence, when they will rent a car, will be for first 3 nights with another family and they are interesting to rent for this part a villa in a nice village and to make day trips from there.

My questions are regarding the part after leaving Florence.

They consider visiting, in 8 days:

- San Gimignano
- Volterra
- Pisa
- Siena
- Arezzo
- Cortona
_ Montepulciano
- Orvieto
- Bagnorecio

They would like to stay in 2 (max. 3 ) places and make day trips.

I hope you can help with advices regarding where to stay, what from above list to visit from each place where we shall stay.
Do you recommend to delete some places in above list or to replace them by another?

Thank you in advance.

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