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Road Trip Through Italy

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I'm just starting to plan a trip to Italy in March/April and looking for some suggestions. It will be my families first trip to Italy and we are carving out about 20 days. I'd love to road trip a loop, so that we can visit several places and not have to pay a one way car rental, but in and out of different cities is also an option. We are a small group of 6, active 60's, to 17 year old. Foodies, wanderers, less interested in museums, more interested local shops, churches, and out of the box adventures. I'm ok with researching hotels and what to do in the various stops, but I'm stuck on where the stops should be.

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