In Two Weeks

Two weeks will give you enough time to see Tuscany's top destinations with some additional time to sample the treasures of Umbria and the pleasures of the countryside. For the first 7 days, refer to "Tuscany in 1 Week" and then move on to Arezzo.

Day 8: Cortona & Arezzo

Aside from the marvels of Piero della Francesca in Arezzo and the bucolic setting around Cortona, the adopted home of Under the Tuscan Sun author Frances Mayes, one of the nicest parts of this day will be the ride between the two. The SS71 is studded with castles, vineyards, and sunflower fields. In fact, finding a nice bed-and-breakfast outside one of the towns will make for one of the trip's most memorable nights.

Day 9: Perugia

The city's National Gallery is a must-see on any visit to Umbria, but just hanging around the cafes of this animated medieval village makes it worth the trip. Central Italy can be rather short on nightlife for young people, but Perugia's university scene makes the city a welcome exception.

Day 10: Assisi

This is the most revered shrine in all of Italy, with the Basilica di San Francesco second in importance only to St. Peter's. It will take the entire day to explore all the city's art, from Giotto's paintings to the recently restored Rocca Maggiore fortress.

Day 11: Todi & Spoleto

Prospective real-estate buyers will be tempted along the vineyard-lined road to Todi, where myriad Americans and Britons have made a second home. The town is one of the most quaint in all of Central Italy, and is worth a quick visit. End the day in Spoleto, home of the country's most famous outdoor festival of the performing arts. By all means, check your calendar to see if you will be there during that time.

Day 12: Orvieto

Two great stops on the road to Orvieto: Chianciano Terme, where you can do like the Roman soldiers and take the "cure" at its thermal springs, and Chiusi, a bonanza of Etruscan urns, tombs, and other impressive remains. Approaching Orvieto in the evening offers you a gorgeous view of the city illuminated by sunset, or spotlights at night, and is an ideal stop for dinner and some of its "liquid gold."

Day 13: Montepulciano & Montalcino

Make your way south along the ancient Via Cassia to Montalcino, and then to nearby Montepulciano. These two wine-producing giants are worthy stops in their own right, even for those uninterested in wine. Nearby is the model Renaissance city, Pienza, surrounded by the kind of captivating Tuscan landscape you see in promotional photos.

Day 14: Depart Florence

Reserve this day for last-minute leather shopping in the San Lorenzo market and to catch whatever sights you missed on the first 2 days.