Cortona, Italy

Driving through Tuscany you can see Cortona long before you can get to it: a city on a hill overlooking the countryside below. We found Cortona on a blustery gray weekday when there were almost no tourists in town. The city is small and maze-like with dozens and dozens of charming shops, cafes, churches, and alleyways to explore...a perfect place to stumble upon on our way between Florence and Assisi.

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