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Help! Mom and daughter Italy trip

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This July I plan on taking my daughter (18) to Italy for her graduation. We are not exactly sure on the trip length yet - 8 to 10 days. Anyways, we have never been to Italy before and would like to make the best and most memorable experience as we won't likely visit again. We get along very well and have similar ideas on what we want to see. We are interested in exploring the history as well as immersing ourselves into the culture. I have several points, though.
1) should we do a guided tour or plan on our own. If so, how difficult and safe would planning our own trip be?
2) we want to see Rome, Venice, cinque terre or Amalfi coast, and Naples (this is a must as we have family history here. We were thinking driving here would be the best bet).
3) any tips/must do's of where to visit, what to do, how to travel, and where to eat would be greatly appreciated!

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