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First Trip to Italy. Need Help on Accommodations in Tuscany

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Hi! We are planning our first trip to Italy this fall. Late Oct - Nov. We will be going to Florence, Cinque Terre, Tuscany and then departing from Rome.

After Cinque Terre our plan is to do 4 days in Tuscany before driving down towards Rome. Wanted to get suggestions on where to stay. Ideally love the idea of staying in a bed and breakfast or agriturismo. Want to have the local experience. We love food and wine. We are in our late 30's and traveling without our kids. So would love a place that is romantic. Would be nice to find somewhere with a view...and even a place where we could walk to town and grab coffee (which I know may be difficult to find). But we do plan on getting a car after we come back from Cinque Terre. So any suggestions on where we can pick a car up would be great too!
Had a friend suggest a couple of places. Le Due Volpi. Loved the reviews. But think the region may be in the opposite direction?? Not familiar with the region so if it is something to explore, we are willing to change and modify plans. (Mugello Region).

Another one that came recommended was Validrose. Again loved the reviews but think it may be too close to Florence.
Wondering if we should stay more Chianti or Siena? But we are completely open to any area. (We do not plan on going to Pisa.)
I've pinned so many places and regions. San Gimignano, Montalcino, Chianti, Siena, Orvieto, Montepulciano, you name it. Its now starting to blend together and get overwhelming but want to book soon!

So now looking at other opinions. Open to suggestions! Thank you in advance!

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