Automatic Translation

Thursday, October 9, 2025

Via Romea Germanica Day 101: Pieve a Sassaia - Cortona

Ero una barca alla ricerca di un porto. Un vascello fantasma senza rotta. Uno spirito e un corpo con luce opaca. Nel cammino ho creduto, nel cammino il mio spirito e il mio corpo hanno trovato luce, pace, sorrisi

(I was a ship in search of a harbour. A phantom vessel with no course to sail. A spirit and a body with opaque light. I believed in the Camino, and in the Camino my spirit and my body found light, peace, and laughter)

- Giovanni Roberto, Templar hospitalier


When the church bells awoke us at 7, I threw open the shutters to see hot air balloons drifting toward us in the dawn light. There is a balloon festival in Castiglion Fiorentino, and the balloons are in the air every day at dawn and dusk!

Our host served us coffee with hot milk, biscuits, bread and homemade jam, then showed us around the little church next to his home and pilgrim hostel, Pieve a Sassaia. The original construction of both home and church dates back to around the year 1000, with alteration and expansion of both in the 17th century. 

After signing the guestbook and leaving our donation in the box, we shouldered our packs and headed out. 





A path through the olive groves, and then through the forest, followed by gravel and paved roads took us ten kilometres to Castiglion Fiorentino, where we stopped for a beer and a pizza under the arches of the 16th-century Loggiato Vasariano.







A bit of history: Castiglion Fiorentino 

Founded by the Etruscans in the sixth century before the Christian era, Castiglion Fiorentino was an important crossroads between Cortona and Arezzo. The Etruscans drained the swamps of the valley to render the land arable, but under the Emperor Augustus the Romans blocked the mouth of the river Clanis, an ancient waterway that no longer exists, because they held the river responsible for the Tiber overflowing and flooding Rome. This destroyed the Etruscan drainage system and turned the Chiana valley back into a malarial swamp. But the town of Castiglion Fiorentino, up on the hilltop, continued to thrive. 



We picked the best table with a view at the bar under the Loggiato, and ordered Belgian beer and a pizza to share for lunch. Here we got talking to Fiona and Jonathan, Australian walkers who are currently vacationing in the area with a few walks thrown in. Nothing too strenuous, as Fiona is recovering from a bone marrow transplant. They had just walked from Cortona, and told us the path was easy and very pleasant. 


After this lunchtime conversation we set off downhill from Castiglion Fiorentino, passing by the 16th-century church of the Consolazione and then through a nursery garden where baby cypress trees are raised.






The sadistic Via Romea Germanica people then marched us up to the top of the hill and marched us down again.... just so that we could pass by the castle visible on the hilltop in the picture. 

Couldn't we have gone around the bottom of the hill instead?






The advantage of walking up to the castle was that we had a great view of Castiglion Fiorentino behind us. And when coming down the other side, we could see Cortona high up on the top of the hill ahead! I was a bit loathe to walk all the way up there at the end of a long day, and in any case we were having trouble finding a place to stay in the town because of the annual Walk for Peace, which takes place this weekend, with large groups of people - churches, Scouts, etc. - all converging on Assisi from different directions, many of them appartently passing through Cortona on the way. They have occupied all the beds in the youth hostel and the various religious institutions in Cortona! In the end we found a room at an agriturismo, or farm holiday place, Il Frantoio, at the bottom of the hill. A bit expensive, but the perfect solution... we can put off the long climb until morning, and the agriturismo serves dinner as well! As the name suggests, Il Frantoio is a fully operational olive oil press, and they just started pressing the new oil yesterday; we sampled one day old olive oil on our bruschette at dinner! 

It's a long way up to Cortona


The horses at Il Frantoio 


One of the many cats at Il Frantoio 

Me at Il Frantoio 

The olive press


The olive oil, on bruschette 

The room



Pieve a Sassaia - Cortona (or almost...) 21.5 km

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