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Advice on Rome/Tuscany/Amalfi Itinerary

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Hello fellow travelers!

I am planning a trip through Italy over 13 nights. My tentative itinerary is as follows:

-Arrive in Rome and spend 2 nights (Sep30-Oct 1)
-Take high speed rail to Florence and spend 2 nights (Oct 2-Oct 3)
-Rent car in Florence and explore backroads to Montepulciano and stay 1 night (Oct 4)
-Drive from Montepulciano and spend another night in another small town, suggestions?! (Oct 5)
-Complete drive to Naples and drop car. Ferry to Anacapri and spend 2 nights (Oct 6-Oct 7)
-Ferry to Sorrento and private car to Amalfi or Positano and stay 4 nights (Oct 8-Oct 11)
-Private car to Naples and high speed rail to Rome for 1 night (Oct 12)
-Fly back to Chicago (Oct 13)

For anyone who has experienced a similar itinerary or has knowledge of this type of travel, I would greatly appreciate any feedback. Does this sound like a reasonable undertaking?

Sincerely, Tim