Tour the caves of Montepulciano
Walk (almost a hike) up to the Fort above Assisi
Tour the churches of Assisi
Walk up the Leaning Tower of Pisa
Dinner in Florence with a walk along the river
Best Way To Get Around:
We rented a car from Avis for the convenience of it. There are cheaper rentals at Rome's airport, but with longer lines. Be careful that you tally in the cost of fuel, which is pricey.
If you don't need to go off the beaten path, we strongly recommend travelling by train. If you haven't been to Italy before, there is SO much to see on the train stops, and trains are much less stressful.