Question on Winery with tour, tasting, dinner and accommodation near San Gimignano/Chianti area


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Our family, 2 adults and 2 children ages18 and 16, is planning to drive from Rome to Florence in August. We would like to see the famous cypress lined roads in Val D'orcia. Where will be the best spots to stop and take some photos? We are thinking to have lunch in Montalcino or Pienza. Any suggestion on where we can have lunch with a glass of Brunello and a great view? Then, we would like to stop by Siena before visiting a winery where we can tour the vineyard and the cellar, learn about the wine and wine tasting, have dinner and stay overnight. Is there any winery with these activities/accommodation around San Gimignano/Chianti area? We plan to leave early morning from Rome and arrive in Florence the next day around noon. Thank you!

You can drive up from Rome and exit in Montepulciano, making your way to Pienza and then on to Montalcino. You'll see these views of cypresses along the way! Gorgeous panoramic views between Pienza and San Quirico d'Orcia and again between San Quirico and Montalcino.
Lunch in Montalcino, so that you can have your Brunello with a view. For lunch, somewhere not in town will offer better views, such as the Locanda Demetra (Podere La Buca, on the road back away from town not in the center) or the ristorante Boccon diVino, on the way up to Montalcino.

You can head on toward Siena and spend the night there. Get to see the town in the late evening, and morning, with dinner there.

The next morning make your way to a winery near Castellina - you can stop by Il Cellese but book ahead so that they are ready for you early - then make your way north through Chianti following the Chiantigiana road SS222 to arrive in Florence by lunchtime.