This itinerary starts and ends 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.
Beyond the Porta al Prato, the Corso leads to the trapezoidal main square Piazza Pio II, a grand and elegant square, surrounded by the city hall, with its bell tower, the Palazzo Piccolomini, Palazzo Borgia and the Duomo.
Pienza has some wonderful views over the Val d'Orcia below. This itinerary ends on the via Via del Casello at the edge of Pienza. Take a final stop at Bar Il Casello (Via del Casello 3), a great spot with uninterrupted views of the Val d'Orcia and frequented by locals and young lovers.
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There is a similar but shorter circular itinerary Anello Pienza - Cappella di Vitaleta (10,2 kms).