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Tuscany leg of trip--floundering a bit

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Hello again. I have two full days allocated to Tuscany (after three full days in Florence). I know it's not nearly enough but it will have to do this go-round. We will be leaving Florence on a Saturday (9/24) and, given the short distance, I hope to get something out of the travel day. I am trying to decide on a base for our three nights in Tuscany. Geographically, Siena makes sense, but I am very open to other towns. San Gimignano and Montepulciano sound interesting to me, but don't seem all that centrally located. Maybe the distances to other towns in the region are short enough that it doesn't matter. I am also trying to decide whether to stay in a city/town, or just near one. I know that driving in the towns can be very limited and difficult. So is it better to stay right outside the town or maybe even just in the general area?

I don't have any set agenda for Tuscany at this point; I'm hoping to keep it relaxed and will try to resist the urge to cram too much in so we can enjoy just being there. I definitely want to visit a winery (or two?), and a couple of the smaller hill towns. It's going to be hard to choose. I have a bit of concern that our full days in Tuscany are Sunday and Monday; will closures be an issue?

We are planning to pick up a car as we leave Florence, and drop the car somewhere on the day we drive to Rome, our last stop on the trip.

Advice related to any of the above would be most welcome! I've been reading Tuscany threads and other people seem to know more what they want to do there and where they want to go. Thanks in advance for your input!

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