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Planning my trip to Italy

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I will be traveling to Rome with a teenager(15) and then have 9 days. Need advice on the logistics and advice on traveling on our own is a better idea or taking day tours from Rome. We would like to stay in Rome for 3 days, go to Florence for 2 days/1nt, then to Venice for 2days/1nt, travel to Naples/Amalfi Coast 2 days/1nt and back to Rome. How would I book transportation from one place to the next, transfers to and from hotel and sightseeing in the city. Open to ideas and suggestions.

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