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Pienza to Venice; Ascoli to Naples

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We are planning a 1 month trip to Italy. The only definite bookings at this time are flights in and out of Rome and the B&B in Positano. My tentative itinerary is to land in Rome, train to Orvieto for 1 night. Pick up car and drive to Pienza for home base for 6 nights. Venice for 4 nights, Bologna for 4 nights, drive to Ascoli Piceno for 2 nights (family), then transit to AC for 1 week and finish up in Rome for 3 nights. I was hoping to drop the car somewhere in Tuscany and train to Venice. BUT, it looks like that is a 6-hour train ride. It seems that driving might be quicker but I am not sure that is our first choice. Any recommendations on the best way to get from the Pienza area to Venice? Then, I am also looking for recommendations for the trip from Ascoli to the AC. I was thinking about driving from Ascoli to Naples airport and then public/private transportation from there to Positano. Would there be a place to drop the car after Ascoli and train to Naples? Thanks for any suggestions you might have!

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