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Tuscany - need help narrowing down a place to stay

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Thanks everyone for all of your help. I've narrowed down our list to a few places and wanted to get your opinion. Agriturismo Marciano and France's Lodge unfortunately were booked. Have also read over Bobs suggestions and others which were extremely helpful. Unfortunately the ones I wanted were not available for our stay. Back to the drawing board!
So we will be going from Florence to Cinque Terre. Then taking a train from Cinque Terre and picking up a car and driving to Tuscany. We will be in Tuscany for 4 days before we head to Rome. Need a place to stay. This October.

It may help to provide My list of places to visit : ( I realize we may not get to all). San Gimignano, Siena, Chianti, Montalcino/Montepulciano, Val d'Orcia, Civita do Bagnoregio, Pienza and Pitigliano. And the list could change -- we are super flexible. I really would like more of a personalized feel- group dinner, breakfast, a farm stay would be great...on a vineyard a plus... And somewhat close to a town to go to a restaurant, etc. I know-- impossible. Do you think we should stay closer to Siena or more south? The hubs thinks near Siena would be easier as a base. Here are some places I am looking at. Let know your thoughts. Open to suggestions.


Closer to Siena:
Villa Castagno
Podere La Strega

Closer to Pienza:
Terre di Nano
Villa Mazzi
Borgo Canalicchio

Is Chianti too far north to be central?
Poggerino
Il Palagio

TIA
Overwhelmed tourist

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