Guided tour of Montepulciano and Pienza

Montepulciano and Pienza

From Pienza to Montepulciano

Piccolomini and Poliziano's hometowns

max 6 hours

medium difficulty

entrance ticket to Palazzo Piccolomini in Pienza (the visit is available upon request)

The guided tour that Cortona Tourist Guide proposes starts from Pienza, the town where Enea Silvio Piccolomini, who became Pope Pius II, was born. This village in the province of Siena is one of the best examples of 15th century town layouts.

The tour of Pienza led by an accredited tour guide will start from Piazza Pio II, which was designed by architect Bernardo Rossellino, where we can see the Cathedral, a building characterised by a Renaissance facade and decorated with works of art that Pope Pius II commissioned to the major artists working in Siena at that time.

Then we will admire other monuments fronting onto the square such as Palazzo Piccolomini, the elegant residence of Pope Pius II famous for its hanging garden from where one can enjoy a stunning view of Val d’Orcia, the Town Hall and Palazzo Borgia.

The guided tour of Pienza will end with a lovely walk along the main street and its nice shops where you can taste and buy all the different varieties of the excellent pecorino di Pienza, a special locally-made sheep cheese having a peculiar flavor given by the clay soils of grazing lands in Val d’Orcia.

In the afternoon we will visit Montepulciano, a popular town situated between Val d'Orcia and Valdichiana. Here, the combination of Middle Ages and Renaissance features creates an extremely charming and elegant town, which is embellished by works of art of great Renaissance architects like Antonio da Sangallo, Baldassarre Peruzzi and Michelozzo.

Montepulciano, hometown of Agnolo Poliziano, still preserves its old layout with narrow and steep streets that contrasts with the largeness and refinement of Piazza Grande, where we will visit the Cathedral and the Town Hall, which was renovated in the 15th century according to the style of Palazzo della Signoria in Florence.

Montepulciano is also the town of Nobile wine, so we can organize wine and local food tasting experiences in the old wine cellars where it was produced in the past.

Every year at the end of August the town hosts the so-called "Bravio delle Botti", a challenge where the eight town quarters compete for winning a prize named "drappellone" by rolling big barrels of wine (about 80 kg each) up the town for nearly one kilometer.

The guided tour of Montepulciano may continue upon request with a visit of the Church of San Biagio, which was built in an pretty isolated and evocative place right outside the town, an incredible example of 16th century Tuscan architecture and a masterpiece by Florentine architect Antonio da Sangallo il Vecchio.


Medium with some uphill stretches (a means of transport is needed to get around in the town surroundings).