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Six Days in Montalcino - help with itinerary

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As part of our two week trip to Italy we’ll be driving from Florence and spending six days in Montalcino at the Palazzina Cesira. I’m hoping to put together a tentative itinerary for visiting the wonderful hill towns. My wife and I spent four days in the area 10 years ago and had a wonderful time, but our travelling companions have never been to this part of Tuscany.

We are thinking of stopping in Volterra for a visit and lunch, perhaps three hours total before heading to our hotel in Montalcino. Does this sound reasonable? Is there a scenic route that you would recommend?

That leaves 5 days to tour around the Val d’Orcia. What would be a useful itinerary considering that we would not want to be too far from Montalcino if we were to eat dinner away (this is more a matter of tricky curvy roads at night than distance). We could easily have a main lunch and a light dinner or the reverse – whichever would accommodate the route for the day. We would want to see Siena, Pienza, Montechiello, Montefollonico and Sant Antimo. Others places I’m not familiar with.

Any help to get started would help.

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