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Cortona to Positano in mid September

This part of our 8 day Italian adventure has me stumped: getting to Positano from Cortona and then getting from Positano to Rome. I feel with enough research in advance and with Google Maps I should be able to get around, but please critique my "plan." I will have a rental car. I was thinking of driving from Cortona and parking it in a parking garage near the Naples train station and either 1) hire a driver to get us from Naples to our hotel in Positano, or 2) take a ferry from Naples to Positano. Being we are only in Positano for 2 nights, I'm trying to do get there as quick as possible to have as much time there in the town. This day of travel actually falls on our anniversary also so it would be nice to get there situated, and relaxed as possible so we can enjoy a romantic, scenic dinner there (would love input on your favorite restaurant for ambiance and food quality.). I haven't come across a direct from Naples to Positano but it does look like you can get there via a few stops. Has anyone does this? I'm assuming it's relaxing and very scenic, but how long does it take from boarding in Naples to departing in Positano? We are fit and in good health so not worried about the steps from the shore to the hotel. 2 days later we'll be reversing this route to get back to the car, and then drive to Rome for a final day. Please offer tips or advice for those that may have done something similar to this.

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We drove from Cortona to Sorrento, dropping our car off at the rental agency in Sorrento (super easy.) If you want to keep your car in Naples then head to Positano, I believe you have to take the train to Sorrento then either a bus or water taxi or private taxi to Positano.