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Florence to Siena(and surrounding area) to Sorrento

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We are planning to stay in Florence, Sorrento, and Rome for a total of 17 nights. We are thinking of shortening our stay in Florence to add a few nights in Siena or somewhere nearby.

Can you recommend any locations/towns to stay in near Siena. I would like something that is close to sights and wineries and restaurants.

Can you please recommend some place to visit near this area? We will be traveling by car.

We plan to spend 2 or 3 nights here.

From this area, we will proceed to Sorrento by train. What train line is best to get to Naples/Sorrento?

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