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I highly recommend Gubbio in Umbria (Italy).

Gubbio was very important between 1000-1300 when it was independent. After that its decline started, and that's probably what kept the town small and contained. I still remember walking inside Gubbio and how it felt so... medieval and different from other Italian towns. I grew up in a small Italian medieval town but Gubbio is quite unique.

http://en.wikipedia.org/wiki/Gubbio



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