Start with morning pickup at your hotel in Rome, then leave the city behind on the 127-mile (204-km.) trip to Arezzo, whose expansive plaza was part of the set for Roberto Benigni’s “Life is Beautiful.” The historic center sustained heavy bombing during the Second World War, but you’ll find wonderful architecture that’s survived through the centuries. See the Church of San Francesco Arezzo, a medieval landmark with a cycle of vivid frescoes that includes 'Legends of the True Cross' by Piero della Francesca, then visit the Arezzo cathedral to see gorgeous stained glass and another Piero della Francesca work, 'Mary Magdalene.'
From Arezzo, continue to Cortona, a hilltop city with a long history. Join the guide for a tour of the places where “Under the Tuscan Sun” was filmed, with plenty of time to see the town’s most beautiful (and unusual) places. One highlight for many visitors is the elegant Bramasole, a key setting in the movie and perfect example of a classic Tuscan villa.
Following your time in Cortona begin the return trip to Rome, where this tour concludes with drop-off at your hotel.