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From Ascoli Piceno to Naples--what are the best options?

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We will be driving from Bologna to Ascoli Piceno in mid-September to visit family. Our next stop is Positano. While we COULD drive to Naples (airport or train station?) I am a bit concerned about driving that route. I cannot seem to find a train route that makes sense. I would appreciate any advice.

As far as Naples to Positano, I am considering a driver but am open to other options for getting from Ascoli to Positano.

Thanks in advance!

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