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Can't choose between 2 itinereary options in Italy

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I need advice! I'm traveling to Italy in early October and can't decide how to arrange my trip. I originally wanted to fly into Venice and work my way down, then departing from Naples, but now that I think about it, I would really like to have the most direct flights possible. And that's not going to happen if I fly out of Naples. This is my first trip to Europe, so I want to make the 'traveling' part of the trip as seamless as possible.

Option 1:

Fly into Venice -- Florence/Tuscany -- Rome -- Sorrento -- fly home from Naples (all of these flight options are early morning, so I would need to leave Sorrento by 7am and they all involve layovers in other European airports which I'm not too comfortable with).

Option 2:

Fly into Rome (arrive at 10am) and take the trains down to Sorrento and arrive by 2pm to start my trip with some beach time -- Rome -- Tuscany/Florence -- Venice (short, direct flight home). Both flights on this itinerary only involve 1 layover in the US and none in Europe.

I would obviously prefer the 2nd option, but am I backtracking too much with this route? Are there logistical things I'm not considering? All travel will be done by train except I will rent a car in Florence to drive into Tuscan countryside.

Thank you!

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