After much research need your reflections on this itinerary. My goal is always to use time wisely and make good connections.
Fly into Florence 4 days
Rent car drive to Volterra, San Gimignano, to Siena - 2 nights here
Drive to Perugia airport, drop off car, public transportation to Assisi
Train to Naples, on to week or more in Amalfi area
My other option is to skip Volterra and San Gimignano and use buses to Siena and Assisi.
We would be doing this in mid to late October,hoping to avoid some crowds.