Your itinerary should begin at the gates of Siena (a city to which one could dedicate page after page) and journey towards the monastery of Monte Oliveto Maggiore. The countryside will be some of the most beautiful you will find anywhere. Dark green patches of cyprus, oak and evergreen top every little hill or mound, often tucked in around a hamlet or an isolated farm house, and alternate with the golden hues of grain, vineyards (remember you are near the famed Chianti region) and acres of sunflower patches that skirt the lower slopes of the hills and completely inundate the valleys lying between them.
Your first stop should be at San Quirico D'Orcia, a tiny medieval borgo. For defense purposes, it was built atop a hill, which divides the Orcia and Asso valleys. Its main attraction is the Collegiata, a simple but extremely moving romanesque structure. Be sure to note the grandiose Romanesque portal (c. 1080) and the late 13th-century lions and caryatids sculpted on the façade.
PienzaLeave the medieval world of San Quirico and journey into the high Renaissance in Pienza. With only a few miles and a few hundred years separating them, it is extraordinary that these two villages are so remarkably different, so clearly representative of diametrically opposed philosophies. Whereas San Quirico is somber and mystical, Pienza is an architectural expression of the humanistic world of the 15th century. A glorious experiment in town planning, it was virtually rebuilt between 1459 and 1462 by the architect known as Il Rossellino, by commission of the humanist pope Pius II (Enea Silvio Piccolomini). Corsignano (as Pienza was originally called) was Piccolimini's birthplace; after elevation to the chair of St. Peter, he decided to transform it into a model town. It is charming. The most important buildings all face onto the central Piazza Pio II: the cathedral, Palazzo Piccolomini (Rossellino's masterpiece, inspired by Palazzo Rucellai in Florence), Palazzo Comunale with its colonnaded portico and elegant tower, and Palazzo Vescovile (Episcopal Residence). A true jewel of the Renaissance.
MontepulcianoOn the 14-kilometer drive from Pienza to Montepulciano, you round yet another bend in the road and there before you, on the opposite side of the valley, w ill be Montepulciano, the town famous for its Brunello. Below it is San Biagio (below), considered to be Antonio da Sangallo the Elder's masterpiece and one of the most significant structures of the Renaissance. Set just outside the southwest wall of town in a quiet pastoral location, its clean lines and harmonious structure (Greek cross with a dome) are a joy to the eye, and although it is quite small it appears to be utterly monumental.
San BiagioYou will remember San Biagio. The walled town of Montepulciano sits just above it, and it's a must. Leave the car at the parking lot inside the walls and walk up the Via di Gracciano (which eventually becomes Via Voltaia). It is worth the stroll if you don't mind seeing Gothic and Renaissance noble structures on both left and right. Piazza Grande is like Pienza's central square: everything centers on it, including the Palazzo Comunale and Duomo with its unfinished belltower. If you have a chance, try to visit the charming little Municipal Museum (Museo Civico) just behind Piazza Grande.
As you wander through Montepulciano's side streets, don't forget to stop and have a sip of its world famous wine, Brunello di Montepulciano. Buy a bottle to take home too.
"Published by and reprinted with the kind permission of In Italy Online."
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