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Overwhelmed with planning! Need help from Italy experts.

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Hi travel friends,

I am planning a trip to Italy at the end of May for 2 weeks. I will be traveling with 3 kids (ages 3, 6, and 8) so am hoping to have great local experiences and be able to enjoy local towns, good food, walk to playgrounds and gelato places and some local markets. I would be happy to share my time between countryside (if short drive to towns) and perhaps staying in an adorable village. We love good food, but wine and vineyards are not the top priority.

I have been to the major cities, so am thinking about Tuscany/Umbria and maybe adding a short Venice trip at the end for my kids to see it.

I am overwhelmed with the number of cute towns. I can't decide between all the towns in Tuscany and Umbria. We definitely want to visit Siena, although I don't think we need to actually stay there.

I know I don't want to drive too far every day and that we don't love curvy country roads:)

I am looking at a place in Marche (through vrbo) , a place in Umbria (called Murlo), and Lilliano.

Would love thoughts on all those places. Any any other highly recommended places or how to narrow it down. And any ideas to make this 2 week exciting trip run smoothly...

Thank you SO much in advance for your help.

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