Siena is a glorious city of winding narrow streets that cling to steep hillsides. It boasts an unmatched, enchanting medieval atmosphere and the buildings surrounding the central Piazza del Campo symbolize the golden age of the city. Between 1260 and 1348, wealthy citizens contributed to a major program of civic development, and the stunning results are still there to enjoy today.

A nasty bout of Bubonic Plague and an 18-month Florentine siege worked to freeze Siena in time, and now most of its medieval buildings have been carefully renovated and restored. Your guided walking tour includes the Church of San Domenico, which contains the relics of the famous Saint Catherine— including her preserved head—and beautiful frescoes by Sodoma in the chapel. The Piazza del Duomo, with its magnificent cathedral in black and white marble, is built on Siena's highest hill. You’ll also visit the Cathedral of Saint Mary of the Assumption with a beautiful inlaid marble floor and pulpit by Nicola Pisano, and the shell-shaped Piazza del Campo with its original 13th-century palaces (the Palazzo Pubblico has been the seat of Siena government since the 13th century).

Nearby is the 300-foot-tall Torre del Mangia bell-tower. You'll have some free time to shop and browse; then, proceed to a local farmhouse where estate wine and olive oil are produced. Taste these and many other products during an Italian lunch, accompanied by local wine. After lunch, you'll have some free time in the town of San Gimignano—chosen by Zeffirelli as the setting for his masterpiece Tea with Mussolini. You may choose to explore the interesting churches, palaces and shops, the Piazza della Cisterna, the Devil's Tower, the 11th-century cathedral and Piazza del Duomo, the Old Podest’ Palace, the 1353 Florentine fortress, or the simple Sant'Agostino Church that hides a heavily decorated Rococo interior by Vanvitelli—architect to the Kings of Naples.