We start from Pienza, ideal Renaissance city planned in the 1400’s by the Pope Pius II, today well known also for the pecorino cheese (sheep's milk cheese) that can be tasted in one of the shops along the main street. From here our walk follows a panoramic road, dotted with cypress trees, the sentinels of the Val d’Orcia. We reach the lovely village of Monticchiello, where we can stop for lunch in a typical trattoria.After lunch we visit the village and the main church with its interesting XIV century frescoes, then we continue along winding dirt roads until we arrive in Montepulciano, the so-called 'Pearl of the 1500's'. The town is also well known for the DOCG red wine Vino Nobile, the 'king of all the wines', as written by the poet Francesco Redi in the XVII century.