In the morning, head to Cortona, the Tuscan hill town made famous by the travel memoir (and later, movie), Under the Tuscan Sun. At your own leisure, or opt to join a guided walking tour (at own expense), stroll the narrow cobblestone streets of Cortona, taking in the medieval atmosphere. Linger in the squares, pop into the Basilica di Santa Margherita and check out the imposing Palazzo Communale.
Or plant yourself at an outdoor cafe to sip an espresso or indulge in a classic Tuscan meal (at own expense). Later, meet up with your guide and hop on the coach for the next part of the tour.
Arrive in Assisi and be prepared to follow in the footsteps of St. Francis, one of the most beloved figures in Church history. Visit the church named after the saint, the majestic Basilica di San Francisco, also the resting place of Francis. See the frescos by late-medeival/early-Renaissance painter Giotto.
When the time comes, return to the coach and begin the journey back to Siena.