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Barbarossa tour: a journey through the places of Popes and Emperors

Exploring the Val d'Orcia with a road bike, in the footsteps of Frederick Barbarossa and Pope Pius II

Through the hills and nature of the Val d’Orcia, World Heritage Site, lives the memory of famous personalities who have made history, such Frederick Barbarossa and Enea Silvio Piccolomini, elected Pope with the name Pius II. Here a tour unfolds retracing the places of their events, between San Quirico d'Orcia, the woods of Castiglione d'Orcia, and Pienza, the "ideal city”.

The route, all on paved roads, can be covered in a single day, or divided into stages to immerse yourself even more in the landscape and history of the Val d'Orcia, pedaling “slow”.

We start from San Quirico d’Orcia, a village located along the track of the Via Francigena and that has always been a stop in it. In the town you can admire works of art and monuments such as the Collegiate Church of the Saints Quirico and Giuditta and the Horti Leonini, admirable 16th-century garden. It was in San Quirico d'Orcia that Frederick Barbarossa met the messengers sent by Pope Adrian IV to make arrangements for his coronation as emperor. Since then, every year Barbarossa returns to San Quirico d'Orcia in a characteristic historical re-enactment that takes place in June.

We stop for a first break in Bagno Vignoni, a spa resort embellished by the striking and unique water square, formerly popular with personalities such as Saint Catherine of Siena and the Medici family.

Once we leave again we reach Rocca d’Orcia and Castiglione d’Orcia, towns of particular beauty nestled among biancane and gullies, erosive formations typical of the crete (clays) of the Val d’Orcia.

From Castiglione d’Orcia we take the route again and continue to climb toward Vivo d’Orcia, ancient site of the Camaldolese Hermitage of the Vivo: we thus reach a place surrounded by woods and best known for its springs of pure water, which flow from Mount Amiata and have long been one of the most important water sources in the area.

The journey as far as Pienza is challenging, buti t allows us to take a refreshing break in Campiglia d’Orcia which, with its fortress, tells us that we are about halfway along the route; in this stretch, the itinerary gives us gradients up to 16% (such as the one leading to the Poggio Seragio pass, at the foot of the Amiata), but the views pay off.

From Campiglia d'Orcia we go downhill along the beautiful and smooth Banditone road and, having passed the Lucciolabella Nature Reserve, we can admire the Quercia delle Checche, the first green monument in the history of Italy. Legend has it that it was the place where witches would gather on the occasion of the sabbath, and history tells us that during the last war it became a good hiding place for the partisans’ ammunitions. 

Past the great monumental oak tree we undertake the climb to Pienza, the "ideal city," which we reach soon. Born, as Pascoli wrote, "from a thought of love and a dream of beauty," Pienza represents an urban architectural jewel that has been declared a World Heritage Site: its particular layout, inspired by standards of elegance and balance, is due to the will of Enea Silvio Piccolomini, or Pope Pius II.

From Pienza to San Quirico d'Orcia the journey is short and easy compared to the previous stretches: along this last stretch we are constantly accompanied by the charm of a unique landscape.


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