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Villa or Hilltop Town?

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Mrs Plastic and I will be driving around wine country in Tuscany in mid-late Sep and are trying to decide where we should stay on our last open night. I am curious if anyone has stayed in a Villa type setting or a Hilltop Town and what the pros/cons might be to doing either?

My first instinct is that it would be easier to drive/park in a villa type setting, but I am worried that at night there might be very little in the way of things to do like what you might find rubbing elbows staying in hilltop type town (of course sometimes that can be a plus as well).

We have toured Tuscany once before and hit places like Montulpuciano, Montalcino, Pienze, Sienna and Volpaia. We are staying on Cortona for one night on the way back to Florence FWIW, so we will get some hilltop type experiences on that stay. We are looking see a few new places and one place on the list would be Volterra since Rick Steves says it is his favorite hill top town...we could stay there(more West)? Or we could make a stop there on the way to some other location that might be better situated to tour a few choice vineyards :) Any suggestions or life experiences would be great. thank you for your help.

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