Historic Centre of Pienza – Pienza loop from Foiano

Historic Centre of Pienza – Pienza loop from Foiano

Moderate

4.0

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riders

Historic Centre of Pienza – Pienza loop from Foiano

02:43

56.1km

730m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: August 15, 2026

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After 11.5 km for 243 m

Waypoints

Start point

Train Station

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11.6 km

Town Hall (Former Pretorio Palace)

Highlight • Historical Site

It dates back to the 13th century, but numerous changes and renovations have been made to date. In 1266 it housed the administrative headquarters of the podestà in office at the time and has remained the administrative headquarters of the local government to this day.

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11.6 km

Church of the Most Holy Annunciation

Highlight • Religious Site

Built around the mid-16th century.
The brick façade has a triangular tympanum decorated with a row of corbels. At the top is a brick bell tower topped by a small dome.
The single-nave interior is distinguished by rich 18th-century stucco decorations.

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24.0 km

Massaini Castle

Highlight • Castle

Among vineyards, olive groves and medicinal plants, stands Palazzo Massaini, a place where nature, tradition, Tuscan food and wine merge.
Source: palazzomassaini.com

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27.9 km

Historic Centre of Pienza

Highlight • Historical Site

Pienza is a small jewel of the Val d'Orcia, known as the city of Pope Pius II, aka Enea Silvio Piccolomini, who was born here in 1405. Pius II, once he became Pope, wanted to transform his humble hometown, Corsignano, in an urban-architectural treasure.
He thus entrusted the total renovation of the village to the architect Bernardo Rossellino and the humanist Leon Battisti Alberti, who in just four years, from 1459 to 1462, defined the harmonious and typically fifteenth-century appearance of what would have been Pienza today.
Thus was born that is now known as the ideal city of author: "born from a thought of love and a dream of beauty", as Giovanni Pascoli wrote.
Due to its peculiar characteristics in 1996, together with the whole Val d’Orcia, Pienza was recognized as a World Heritage Site.

Walking through the historic center, in Piazza Pio II, a visit to the Duomo, the Cathedral of the Assumption, is a must. Inside it houses important and remarkable paintings by the most renowned artists of the time, while the beautiful octagonal bell tower rises above the ancient crypt.

In front of the Cathedral you can see the Palazzo Comunale, a historic building dating back to the mid-1400s with its main feature: the large loggia on the facade. Also in the main square, the imposing Museo-Palazzo Piccolomini stands out with its hanging garden from which you can admire a truly unique panorama over the entire Val d'Orcia, from Montalcino to Monte Amiata. To complete the closure of the central square, you can visit the Palazzo Borgia, seat of the Diocesan Museum of Pienza.

Inside the former San Carlo conservatory, there is now the Archaeological Museum of Pienza, a building of medieval origin, with archaeological and Etruscan collections on display and an exhibition itinerary that documents the urban and architectural history of the Pienza area.

A few steps from the historic center, a short walk takes you to the Pieve di Corsignano: a Romanesque church with three naves, whose origins date back to the 7th century.

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27.9 km

Pienza

Highlight • Settlement

A medieval city, awarded by UNESCO as a World Heritage Site. You can enjoy some old churches and palaces here or simply stroll through the atmospheric streets. Also the view from the city wall is great.

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28.1 km

Pienza Historic Center and View of Val d'Orcia

Highlight • Historical Site

Immersed in the green heart of the Val d'Orcia, Pienza stands before your eyes like a Renaissance monument solidified over time. Pope Pius II wanted it and built it as an ideal city, and since then its beauty has been preserved intact. As you stroll through its silent streets, savor the serenity and beauty of a village where art and history blend with the breathtaking Tuscan landscape.

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28.7 km

View of Monte Amiata from Pienza

Highlight • Viewpoint

This is a very scenic route.
Continuing towards Viale di Circonvallazione, SS del Monte Amiata and then SC della Pieve, you will arrive at the crossroads to take the gladiator's cypress trail, a famous stretch of trail in the final scene of the film.

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