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Slide 6 of 14

San Gimignano

You could take a day trip to this towering town, but it's definitely worth staying for a couple of days. Spend time exploring shops and museums — and climbing some of the village's 14 medieval towers. Once you've gotten a workout and enough pictures of the rolling green hills, reward yourself with gelato and a glass of one of Tuscany's many wines.

Image Source: POPSUGAR Photography / Sara Cagle