Pienza was rebuilt from a village called Corsignano, which was the birthplace of Enea Silvio Piccolomini. You can visit this beautiful small renaissance town designed as an ideal city after your walk. The Via Il Casello 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.

Start

San Quirico host a handful of good restaurants. This itinerary starts at one of them, Osteria Il Garibaldi, hidden behind a Tamoil gas station along the Via Cassia. (This is the starting point on the map above and of your gpx tracks).
From San Quirico d’Orcia and Osteria Il Garibaldi, walk south along the via Cassia (Strada Regionale 2), turn left at Via Cerrecchio and then, immediately beyond a farm, take the dirt road to the left. Now we proceed for about 2,5 kilometer and reach the Cappella di Vitaleta. 

The Vitaleta Chapel on the way from San Quirico d'Orcia to Pienza [2]

This chapel, surrounded by a few cypress trees and a farm is among photographers one of the most popular spots. And this is for a reason.

Next stop is the Pieve di Corsignano, a small Romanesque church, and one of the few remains of the original village of Pienza, originally called Corsignano. This last track, going upwards to the church is steep. In front of the pieve is a nice fountain, a good opportunity to refresh yourself for the final stretch.

This itinerary ends on the via Via del Casello at the edge of Pienza, offering some wonderful views over the Val d'Orcia below. Via del Casello has four very picturesque streets that connect to the course: Via della Fortuna, Via dell'Amore, Via del Bacio and Via Buia. Take a final stop at Bar Il Casello (Via del Casello 3), a great spot with uninterrupted views and a place frequented by locals and young lovers.

Download gpx tracks here

There are two other itineraries, one starting from Pienza Anello Pienza - Cappella di Vitaleta (10,2 kms), another starting from San Quirico d'Orcia Anello San Quirico d'Orcia - Capella di Vitaleta (8,64 km).

 

Bar Il Casello

Bar Il Casello
Via del Casello 3, Pienza