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Drive from Rome - Siena- Florence

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We are thinking of hiring a car from Rome and driving to Siena. We want to take a night halt at one of the towns with panaromic views. and then continue to the Pienza, Montalcino Montepulciano.

Day 1 leave rome. I need help to choose which route to take and where to stay ovenight.. Should it be Rome- Spoleto-Spello- Cortona
or Rome-Civita-Orvieto
What we would like do experience: Scenic Country side with rolling mountains...stopping in small towns to have wine or coffee or quick meals. Not much intereseted in architecture and museums.

Day 2: Explore Pienza, Montalcino Montepulciano. Reach Siena by 5. Overnight at Siena.

Day 3: Siena- Chianti countryside-Pisa-Florence
or Siena- San Gimignano- Voltera- Pisa- Florence

Please suggest. I would also welcome a radically different opinion on the driving route. But we would definitely want to do Pienza, Montalcino Montepulciano

We will not be driving inside the cities of Rome and FLorence. Month of travel: June

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