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Driving From Orvieto to Seina

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Hi Foderites. I have 3 questions about driving around Tuscany as it will be the first time renting a car in Italy.

1. We will be renting a car in Orvieto and dropping it off at Pisa Airport 4 days later. I was wondering before I commit to a certain car company if there is a preferred company choice for dropping off at Pisa? I see some companies are not right next to the airport and we have a flight leaving at 10:30 am so I want to make sure we have plenty of time.
2. We will be driving from a night in Orvieto to Siena. Does anyone recommend a parking location outside Siena?
3. For the drive from Orvieto to Siena I am getting overwhelmed by the choices of places to see. I was thinking of Civita di Bagnoregio. Is there anyone who has done this drive that can recommend any good stops heading this direction? We enjoy wandering around, good food and wine and taking photos. We will drive to other hill towns on different days going other directions from Siena. Any suggestions on towns within a few hours of Siena would be lovely.

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