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Hill Towns

In the middle of our Italy trip this July we will be staying for 8 nights in Montepulciano. We hope to use that as our base for exploring several hill towns. We have 9 towns on our list including: San Gimignano, Volterra, Orvieto, Cortona, Montalcino, Pienza, Pitigliano-Grosetto, Civeta di Bagnoregio, and Arezzo. Are there any other must see towns that we should add. Not sure how many to attempt in the 8-9 days we have.

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I assume you'll have a car.

Assisi, for sure, though I don't define anything as a must-see. It's all about the time you have and your interests.

I've wanted to go to Gubbio but have never made it.