Just across the border of the Val d’Orcia, but still within the spectacular panoramic scenery of this World Heritage site, lies the medieval town of Montepulciano.
The perfect starting point to begin a visit to the historical center of the city of Montepulciano is the Sanctuary Sant'Agnese. There are parking facilities for cars and motorbikes on Piazza Lucangelo Bracci Testasecca, Piazza Sant'Agnese or Piazza Don Monzoni, all in the neighborhood of the Sant'Agnese Santuario.
We enter the city through the Porta al Prato. Between the two gates runs the town’s main street, the Corso, whose name is appended in turn to Via Gracciano, Via di Voltaia and Via dell’Opio.
The town offers many interesting medieval and Renaissance churches, and buildings to explore along with narrow side streets and alleyways that take you to magnificent viewpoints of the surrounding countryside. From Piazza Grande, go down following Via Ricci until you get to an intersection of three streets. Turn left under an arch where you should see a sign, San Biagio, and keep walking down to an arch, one of the former city gates.
A steep 20-minute downhill walk from Porta dei Grassi takes you to the photogenic Chiesa di San Biagio, a travertine Renaissance church designed by Sangallo in the XVI century. From here you walk through the overwhelming scenery of the Val d'Orcia towards Monticchiello.
For a detailed excursion through the historical center of Montepulciano, see Walk in and around Montepulciano, with several chapters,
From the Church of St. Agnese to the Church of St. Agostino and the Torre di Pulcinella;
From the Church of St. Agostino up to the main square, the Piazza Grande;
Walk from Pozzo dei Grifi e dei Leoni to the beautiful church of San Biagio on the outskirts of town;
From the Church of San Biagio back to Piazza Savonarola and the small piazza above the Porta al Prato.