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Scenic route from Montepuciano to Siena

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We are going to Italy for the first time this August. Can you please recommend us a great scenic route from Montepuciano to Siena or Siena to Florence? We have always heard beautiful things about the Val d'Orcia Valley and really want to see in all its glory. Also, what are some good wineries around the area?

Here is our itinerary:
Day 1 Rome
Day 2 Day trip to Almafi; Stay at Rome
Day 3 Drive from Rome to Montepuciano-Siena; Stay at Siena
Day 4 Siena - Florence; Stay at Florence
Day 5 Florence-Venice; Stay at Venice
Day 6 Venice; Stay at Venice
Day 7 Venice -- Fly back to London
We will be renting a car for our entire trip.

If you can offer any advise on this itinerary that would be really fantastic. We would really appreciate on some tips and thoughts!

Thank you in advance :)

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