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Stay in Crete Senesi or Val D’Orcia as a base in Tuscany?

In terms of scenery, which one is better for the typical Tuscany winding roads on hills with cypress trees? Crete Senesi or Val D’Orcia? We are trying to choose a base for four days. Found one agriturismo in Serre di Rapolano and one in Pienza. Couldn’t decide.

Also, how is the summer heat in July in Tuscany? Tolerable? Is it better to stay in a lodging with air conditioning? I found not many agriturismos have AC. Thanks in advance!

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I lived half of my life in Florence (and visit there yearly) and I don’t think there is a place in Tuscany without winding roads with cypress trees.
If you are referring to the specific iconic road pictured below, it’s in Monticchiello.
https://images.app.goo.gl/ZpxvEzhoB7iAK3tS7
To take that photo you you have to drive to this exact place:
https://goo.gl/maps/R2kA7mAoUv48oMqAA
This spot is 15 min from Pienza and 45 min from Serre di Rapolano.
Regarding the choice you mention, Serre di Rapolano and Pienza are just 30-35 min apart, Serre di Rapolano is closer to the freeway, so it might be more convenient if you plan to make lots of day trips to various Tuscan (or Umbrian) towns. But Pienza and the surrounding area is also gorgeous, so it’s up to you. I would choose based on which accommodations you like best.