This itinerary starts and ends at the Piazza Dante Alighieri, or at the Porta al Prato in Pienza. Pienza was rebuilt from a village called Corsignano, which was the birthplace of Enea Silvio Piccolomini. You can visit this beautiful small renaissance town before or after your walk.
Just inside Porta al Prato, the main street or Corso leads you to Pienza's central square the Piazza Pio II. Enjoy this brief passeggiata through the ideal city. It was in this Tuscan town that Renaissance town-planning concepts were first put into practice after Pope Pius II decided, in 1459, to transform the look of his birthplace Corsignano. This new vision of urban space was realized in the superb square known as Piazza Pio II and the buildings around it: the Piccolomini Palace, the Borgia Palace and the cathedral with its pure Renaissance exterior and an interior in the late Gothic style of south German churches.
Take the street left of the Duomo, and walk through the Porta al Santo, 43°4'34"N 11°40'46"E, and turn right onto Via di Circonvallazione. A 11-min walk will bring you to the Pieve di Corsignano.
On the Via Santa Caterina, take a final stop at the Unesco World Heritage sign and marvel at the wonderful panorama that overlooks the trail and Monte Amiata.
Continuing down the valley, you will reach the Capella di Vitaleta.
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You can also consider expanding your walk to a longer itinerary, the Anello Pienza - Cappella Vitaleta - Spedaletto (22 kms).