Tour of Cortona, Montepulciano and Pienza, the villages of wonders

The charm of the Tuscan villages

This guided tour of Cortona, Montepulciano and Pienza takes place over a whole day among some of the most beautiful and famous Tuscan landscapes, to discover 3 magnificent towns rich in history, art and cultural, gastronomic and winemaking traditions.

You will be amazed by the architectural elegance of the Renaissance palaces and churches, by the genuineness of the inhabitants, by the charm of the narrow streets and squares of the villages animated by real life.

You will cross the splendid landscapes of Tuscany, of absolute and timeless beauty, including that of the Valdorcia, -included by Unesco as a World Heritage Site.

Ancient villages of Etruscan origin and jewels of the Renaissance

The Tuscany of hilltop villages rich in art and magnificent landscapes is the most suggestive imaginable.

The local guide who will accompany you will let you know the secrets of these ancient villages of Etruscan origin such as Cortona and Montepulciano and will introduce you to the knowledge of the excellent wines of the area by leading you inside the cellars of a sixteenth-century noble palace, narrating local stories and traditions.

He will introduce you to Pienza, the ideal city wanted by Pope Pius II Piccolomini – who was born there – to give life to a dream of beauty and harmony.

Un tour guidato di Cortona, Montepulciano e Pienza nella stessa giornata

The tour is designed to start from Cortona with its magnificent historic center and rich cultural heritage.

We will then move across the Valdichiana to reach Montepulciano with its narrow medieval streets that climb up to Piazza Grande with the Cathedral and the Palazzo Comunale. The visit to the ancient cellars of the buildings is very suggestive, where the Nobile di Montepulciano wine is still aged according to tradition. Leaving Montepulciano, the Temple of San Biagio is worth a stop, one of the most beautiful churches of the Renaissance in perfect harmony with the landscape.

Third and last stage will be Pienza. Entering the ancient walls and strolling among the shops where the famous Pecorino cheese is sold, you arrive at the splendid square overlooked by the Cathedral and the Renaissance Palazzo Piccolomini, the ancient residence of Pope Pius II with a courtyard and roof garden

Walking through the narrow and romantic streets of Pienza you finally reach the famous balcony from which you can enjoy the splendid view of the Valdorcia landscape declared a World Heritage Site by UNESCO.

Tour Details

What you will see

  • Piazza Garibaldi in Cortona with its incredible view over the whole Valdichiana
  • The church of San Domenico in Cortona
  • The historic center of Cortona with Via Nazionale, Piazza della Repubblica with the Palazzo del Comune, Piazza Signorelli with Palazzo Casali, seat of the MAEC (Museum of the Etruscan Academy and of the City of Cortona) and San Francesco
  • The Cathedral of Cortona
  • The historic center of Montepulciano with Piazza Grande with the Cathedral, the Municipality, the elegant Renaissance palaces Contucci and Tarugi, the well of the Griffins and the Lions and the sixteenth-century cellar of Palazzo Contucci.
  • The temple of San Biagio in Montepulciano (exterior, subject to time availability)
  • The historic center of Pienza with the via della Fortuna and via dell’Amore
  • The balcony of Pienza from which you can enjoy the splendid view of the Valdorcia landscape declared a World Heritage Site by UNESCO.
  • The Cathedral of Pienza with its very bright interiors on which the gold of the Renaissance altarpieces shines
  • Palazzo Piccolomini, former residence of Pope Pius II with courtyard and hanging garden (exterior)

Expert guide and art historian

History, art and architecture tours