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Family trip to Italy with a daughter 17 and son 14

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We are planning a trip to Italy for a total of 20 nights. Part is to visit family part sightseeing. We are thinking to fly into Milan, go to Turin maybe 2 nights (we have family there but possibly need accomodation). Move on from there to a small village Camagna Monferrato for 4 nights (we have a family house there). From there to Piacenza (more family) 2 nights (need accomodation). On to Venice (more family) 2 nights (need accomodation). Fly to Reggio Calabria for 4 nights with family (no accomodation needed). Then fly to Rome for another 4 nights to spend on our own. That leaves another 4 nights to fill. In Rome we plan a tour to Naples and Pompeii. In Venice we would like to also fit in Gardaland. Pisa, Siena, Florence and Assisi all appeal. But we don't really have an idea of an itinerary. Does anyone have any ideas? Also accomodation recommendations for a family of 4. I am the only one who has been to Italy but I was a child so I'm not sure that counts.

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