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Trying to decide where to stay in Tuscany

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As part of our vacation to Italy in October, we'd like to stay in Tuscany for four nights. I'm leaning towards the Val d'Ocia region but having a hard time deciding on the particulars, mainly whether to stay in town or out in the countryside. Any thoughts from those who have done both? My ideal would be to stay in an agriturismo, but I also like the idea of being able to walk somewhere for dinner, etc. There don't seem to be many agriturismos within walking distance of a town, but I have found a couple that look close.

Second, any thoughts on Pienza vs. Montalcino vs. Montepulciano as a base? They all look great. Or any smaller towns in the region we should consider?

Thanks!

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