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Arezzo to Volterra, Volterra to Val d'Orcia

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I am planning a trip to Italy with my friend who has a truffle festival visit at the top of her list. I have Val d'Orcia as mine. Is it possible to drive from Arezzo to Volterra, attend the truffle festival Oct 22 (maybe side trip to San Gimignano?), and then spend the night outside of Siena? The next day would be traveling through Val d"Orcia with possibly another overnight stay, then returning to Arezzo Oct 24. Any suggestions would be greatly appreciated!

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