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Where to stay in Southern Tuscany area

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We are driving from Venice and looking for a place to stay in the southern Tuscany area. We will be staying 3 nights and then driving to Orvieto for one night/two days ( with a trip to Civita di Bagnoregio from Orvieto), returning the car and taking the train into Rome.

Is it better to base in Siena for the three nights or find a location around some of the smaller hil towns ? We'd like to explore towns by day but be able to come back and walk around, eat and settle for a drink.

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