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Traveling with Teenagers in Tuscany

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I will be traveling with 3 families to Italy in August - 6 "kids" ages 16-18. My family is planning the section Venice/Tuscany. Venice has been a breeze, but I could use some help with Tuscany. We will be at Hotelito Lupaia, near Montepulciano with 3 rental cars. Anything out of the ordinary to keep the teens interested would be great. To give you some context for our trip so far - we will have bicycled in Florence, gone on a scavenger hunt in Venice and I will locate geocaches in each town we visit. Thanks for your suggestions!

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