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Rome to Positano via Pompeii?

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I am traveling to Rome in early June with my 13 yr. old daughter. I am thinking we will stay in Rome for 3 nights then go to Positano. My questions are: does it make sense to take the train from Rome to Naples, change to the Circumvesuvia train to Pompeii- can we store our luggage and is it easy to find a good english speaking guide at Pompeii or do I need to book a guide in advance?
Also- should we train back to Naples and hire a driver to our hotel in Positano or can we take a train to Salerno then the ferry to Positano? This seems like a lot of planes, trains and automobiles (haha) and logistics for one day??
OR- should we just blow off Pompeii en route to Positano and go straight to Positano (from Rome), then go to Pompeii the next day as a day trip??
And another thing...I have heard that Herculeneum is actually more interesting than Pompeii??
It seems the more I read the more I get confused, so many great sources of info these days. Thanks for any advice you can give!

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