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How long to stay in each city in Italy?

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My husband and I are going to Italy. We are only going to be there 2 weeks and would like to see as much as possible. I have a route picked but think it may be a little abicious for a 2 week trip. I have no idea how long it would take and how long to stay in each place. I dont know if renting a car would be better or buying train tickets. The route is Rome to Florence to Pisa to Milan to Venice to Naples and back to Rome. PLEASE HELP.
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Car service from Naples airport to Positano
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