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If you were cooking up the best Tuscan town for a kid-friendly vacation, Siena would have all the ingredients. Sprawling piazzas that practically demand pickup soccer games, boulevards lined with independent shops and cafes, and stunning art and architecture to impress the whole family mean that Siena is worthy of a full day, if not a longer stay to take it all in. A guided walking tour of Siena’s historic center is ideal, and be sure to experience the famed Duomo with your guide so you don’t miss some of the intricate details. Our favorite kid-friendly resort in Siena has just as much storybook appeal as the town itself. We can also recommend private villa rentals nearby for those who prefer a more independent accommodation experience.

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