Fly to Venice and spend 4 nights in Dorsoduro near the Guggenheim.
Train to Florence for 3 nights in the area near the Basilica SM Novella...
One day traveling to Sienna traveling by bus
Train to Vernazza for 2 nights. Walk to Corniglia and by train to the balance of the 5 villages
Train to Orvieto and rent car
4 nights in Agriturismo outside of Bagnoregio
Visit Orvieto, Bolsena, Civita di Bagnoregio, Lubriano, Viterbo, Tarquinia, Montepulciano, possibly Spoleto
Train to Rome for 5 nights in Trastevevre before returning to the US.