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Logistical help needed

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I am planning our return trip to Italy after a 4 year absence. What I know is that we are flying into Rome. The must sees this trip are: Venice, Emilia Romagna (foodie tours), Ascoli Pisceno ( visit with family) and the Amalfi Coast. We are planning a month's stay and the airport we fly out of depends on where we end up. We would like to stay a week on the AC and perhaps a week in southern Tuscany. We spent 4 days in Florence last visit and while we loved it, we could forego a return visit this trip. I am thinking we will spend about 4 days in Rome once we land. The dilemma is do we then go to the AC, then move north or do we do the northern route and then head to the AC.? I see a car while in Tuscany and know we will definitely need a car to get to Ascoli. We will only spend about 48 hours in Ascoli. I guess the main question is the trip from the north to the AC or from the AC to the north. If we do Tuscany we might drop the car for the ER and Venice portion. We would then need a car to drive from Venice to San Marino (another must) to Ascoli. We could then drive to Rome( 3 hours) then take public transport and fly out of Naples). If we start the trip on the AC, I am having trouble figuring out the rest of the route. Any suggestions would be appreciated!

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