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Itinerary for first time trip to Italy

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Hey everyone!
I know that this question pops up all the time. I’ve tried to plan my trip to Italy by myself (which I usually do without problems) but this time after few travel guide books I’m lost. There is another reason. I haven’t been to EU 25 years and I cannot use my traveler’s experience because I don’t sense EU mentality and culture. Is it possible that somebody will help me to plan this trip or just give me some pointers?
I will travel with family 2+2 (11 and 20). Wing to Venice on August 25, 12 and return from Rome on Sept 12. (19 days). I already made a reservation for 2 nights (Aug 25, 26) in Venice and rented a car for Aug 27. The rest is open. I would like to visit major tourist attractions, explore Tuscany (rent a condo, BB, hotel?...use it as a base to see Florence, Siena, Pisa, Lucca, Cinque Terre on one day trips?). It will be nice to go as far as Naples and Pompeii. Return to Rome for 2-3 nights and fly home. Thanks in advance for all your help.

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