Montepulciano rises on a happy balcony between the Orcia Valley and the Valdichiana Valley, immersed in a splendid landscape characterized by fields, woods, olive groves, and most of all by well-kept and precious vineyards. The notoriety of Montepulciano is in fact linked to the Nobile Wine of Montepulciano.
Original settlement of the late-Etruscan castrum, it became the base for the development of the late-medieval inhabited area called “Sasso”. For its innate particular nature and most of all its position, it was considered to be of strategic importance. Montepulciano soon became object of expansionist aims and of dispute by the major Tuscan powers, both Siena and Florence. Later, in the 15th century, Montepulciano was subject to a process of urban upgrading carried out by the Florentine dominions, and from this upgrading came to be Piazza Grande and Palazzo Comunale, both works of Michelozzo, who managed to make humanistic architecture and Gothic taste live together in harmony. In the following century there was another redesign of the urban structure, with the assistance of great names such as Antonio da Sangallo il Vecchio, Vignola, and others. For the rest, although the village is narrow among the old fortifications of the Middle Ages, one of the principle characteristics is the lavishness of the Renaissance buildings, “signed” mostly by the genius, Antonio da Sangallo il Vecchio.
The Porta a Prato or Gracciano, this, too, restructured in the 16th century, is today home to a wine cellar, which, located near the main entrance to the city, seems to symbolize exactly that you have entered into the “city of Nobile Wine”; it is a very inviting entry also because of the view over the surrounding green hills that you can enjoy climbing towards the inhabited center. Above all else, the presence of the various wine cellars is the recurrent element of a walk in Montepulciano, and it is to be said that the various owners have managed to make their businesses of great cultural interest, too, in so much as allowing (for free) entrance into the cellars, where, among enormous oak barrels and the exhilarating scent of wine, true mazes unravel under the ground of the city with often entire attractive medieval environments being hidden here. These businesses are situated right on Via di Gracciano, principle artery of the old city that, going uphill, actually drives to the visit of Montepulciano, also with picturesque derivations. It is worth entering the side street, Via delle Cantine, which, being entirely curved, immediately you are sent back into a most exquisite medieval atmosphere. Going back to the main street, attention goes immediately to the late-Renaissance Palazzo Avignonesi, designed by Vignola, which presents an ample travertine façade on which open two orders of windows and a large portal framed by a radial rusticated ashlar-work and bordered by lions’ heads. Other relevant buildings of Via di Gracciano are surely Palazzo Tarugi, the 16th-century Palazzo Batignani, Palazzo Cocconi, and Palazzo Budelli, whose peculiarity is a plinth in which are fragments of Etruscan and Latin walls. Dating back to 1285, but entirely renovated in the 1400’s is the Church of Sant’Agostino whose façade, made by the employees of Michelozzo, combines late-Gothic and proto-Renaissance elements
Before reaching Piazza delle Erbe, once headquarters of the 16th century markets that here merged with the valleys beneath, still going along Via di Gracciano the beautiful Palazzo Buratti-Bellarmino (with atrium and inside decorated by frescoes attributed to Zuccari) stands out and the Arch of the Gavina opens, while in the following widening are the 16th-century Logge del Grano, with three round arches. Following along the principle road, that now becomes Via di Voltaia, you will meet the elegant Palazzo Cervini with its singular U-shape design (from the second half of the 16th century based on the design of Antonio da Sangallo il Vecchio) and numerous other buildings of medieval origin but visibly restructured in the 17th and 18th century. Having reached the outskirts of Poliziano Theatre, dedicated to the poet that was born here, a side street, Via delle Farine, descends to Porta delle Farine, from the 13th century, which offers a splendid view of Valdichiana. Near Via del Poliziano is the house of the poet (Casa del Poliziano), of 14th-century origin, and at the end of the street you find the coeval Church of Santa Maria dei Servi, located in a panoramic position over the vineyards that encircle the crest: it has an austere travertine gabled façade and a notable cuspidate portal. By means of a pleasant walk that goes around the wall you reach the Fortress, risen on the remains of a pre-existing castle of the Early Middle Ages (erected perhaps on the site of an ancient temple dedicated to Mercury), rebuilt in 1200 and restructured by Antonio da Sangallo di Vecchio.
The long and interesting visit into the history and artistic jewels of Montepulciano almost reaches an end in its fulcrum, the wide and scenic Piazza Grande. Profoundly transformed between the 15th and 16th century according to architectural and urban Florentine and Roman taste, here several of the most important buildings of Montepulciano stand out. To begin with the Duomo, which rises on the ancient site of the Pieve di Santa Maria, constructed between the 16th and 17th century by Ippolito Scalza. It presents an unfinished gabled façade with three portals and three windows (unfortunately spoiled by an ugly modern bell tower). The interior, Latin cross pattern with three naves, holds different works of art, including the unclaimed Statue of Bartolomeo Aragazzi, a 14th-century baptistery fountain by Giovanni di Agostino, and a 15th-century Triptych by Taddeo di Bartolo. To the right of the Duomo is the austere Palazzo Comunale, partially rusticated and redone with embattled tower at the center, typical Florentine style like Palazzo della Signoria. It was built in the 1300’s near a pre-existing building and was restructured in the 15th century by Michelozzo; so the Renaissance elements, such as the tower, windows and frames, merge with those of the late-Gothic era, such as the raised rusticated ashlar-work; also famous are the internal 14th-century courtyard formed by logge above columns. From the tower you can admire a splendid and vast panorama that spans from the roofs of the city to the surrounding countryside, from Siena to Monte Amiata, from the Umbrian Mount Subasio to large Trasimeno Lake. In front of Palazzo Comunale is Palazzo del Monte Cantucci, begun by Antonio da Sangallo il Vecchio in the 1500’s, and completed in baroque style. It is then the face of the late-Renaissance Palazzo Nobili-Tarugi, probably by Antonio da Sangallo il Vecchio or his student, and of Palazzo del Capitano del Popolo (today headquarters of Nobile Wine of Montepulciano and the umpteenth inviting wine cellar), which shows its medieval origins with its beautiful Gothic forms, and finally there is the Well of the Grifi and Lions, bearing symbols of the city and those of Florence.