Riding through the valleys and over the hills of Tuscany, Umbria and Marche.
At least once a year we make our way down to Castiglion Fiorentino (Arezzo, Tuscany) to visit our dear friend Carlo and his family. Castiglion is one of the little towns in Tuscany you’ve probably never heard of with perennial hotspots, Florence and Siena, not too far away. Castiglion has a rich history though, dating back to the 10th century when it was a papal state called simply, Castiglione. Towards the end of the 13th century, the town was lost in a battle with the Republic of Florence and renamed Castiglione Fiorentino. The town’s name would change over the years as it was repeatedly conquered and re-conquered from much bigger cities like Arezzo to the north, which renamed it Castglion Aretino and Perugia to the south, which called it Castiglion Perugino. It was finally seized and controlled by the Republic of Florence yet again in 1384, which then renamed it Castiglione Fiorentino. Recently, there was a discovery of an Etruscan temple found underneath one of the towns churches that dates back to the 4th century BC. The Etruscans were an ancient civilization with settlements in central Italy. Despite its storied past, Castiglion is perhaps best known as the home town of two legendary Italian figures: Oscar winner Roberto Benigni and Enduro/Dakar specialist Fabrizio Meoni, whose motorcycle shop lives on today even if he is no longer with us.
The road leading from Castilgion Fiorentino towards Carlo’s house continues up the hill to La Foce restaurant – its highest point – then back down the other side, ending at the town of Palazzo del Pero. This stretch is known locally as “La Foce”, often used by locals to circumvent the longer drive through towns and main roads to reach Castiglion. Incredibly, Carlo has this usually deserted mountain pass-like road in his backyard. With incredible views of the valley below, a mix of tight, medium and sweeping corners and just enough height to make the guard rails respectable, this road could be in Anywhere, Tuscany. In the video below, I start out from Carlo’s courtyard, looking out at Castiglion Fiorentino in the distance, then ride up to La Foce and back down the same way. A note on the soundtrack: Carlo had introduced me to this great track, “A New Error” by Moderat, which we had on repeat almost the entire time.
La Foce was my intro into what would be a bit of a tour around central Italy. In my typical style, I wanted to go somewhere I had never been before and so I looked at a map and saw a town called, Città di Castello, which sounded interesting. After descending La Foce and reaching Palazzo del Pero, I made my way onto regional road 221. The ride was unexciting but pleasant. If it weren’t for storybook towns like Monterchi to garnish the route with some medieval architecture/building, I almost would have regretted this destination altogether.
Below, a little video of the ring road encircling Monterchi.
From Monterchi, it was short order to Città di Castello in Umbria for a break and some water and what I thought would be the end of my ride. However, with plenty of light left in the day, I took to my phone and mapped out a route to the town of Acqualagna, via mountain pass SP257 which looked like a lot of fun. Having just replaced my front tyre the day before with a Pirelli Diablo Corsa, I figured this was just the road to break it in. And it was, full of tight, second gear corners the whole way. Although, with no particularly fascinating views on offer, it felt like a road you really had to wrestle with and in that heat – it was 35 ºC in the shade – it killed the fun of it. Finally descending towards Piobbico, now in region of Marche, and the landscape changed dramatically. Riding through a valley now, I was surrounded by red, rocky mountains jutting out from otherwise rainforest green hills. From there it was a short sprint up to Aqualagna, a forgettable little town.
So I’m sitting at a road side cafe in Acqualagna, now a good two hours away from Castiglion, and I was dreading going back the same way. So Maps out again and I found the SS73bis, a road just north of where I was and one that seemed much easier a ride if not for a bit of mountain twisties towards the end. In order to reach it I had to head towards Urbania, a town I learned everything about from its road sign.
Now on the 73bis and it was immediately serene. The sun was just starting to set however, the landscape seemed to have autonomous control over its hue and saturation. As in the dimmer the sky became, the brighter the surrounding colors shone with green greens and yellow yellows. There was a quiet too, about the place, as if the adjacent hills were wrapped in sound deadening foam and the wind blew in whispers. I’m no Buddhist, but this was the closest thing to zen I’ve ever experienced. I almost didn’t even film this section, straight and flat through a valley, but near the town of Mercatello sul Metauro (the river) I pulled over to start the video below.
The road soon became mountainous just after passing Lamoli but not as fatiguing as the 257 earlier in the day. It did provide some amazing views though which made it difficult to ride without constant distractions and stopping for photo-ops. Below is a view from Località Trabaria, before reaching San Giustino.
Leaving San Giustino behind, I took a wrong turn somewhere and ended up near this lake called Montedoglio near Sansepolcro. It was a good thing too because from there I found Via Libbia, the dead straight road, which leads up to the walled town of Anghiari. Important for its strategic position and great vantage point perched up on a hill, Anghiari was the scene of a great battle in 1440 between the Visconti armies of Milano and those of Florence. So great, in fact, that it inspired a fresco painted by Leonardo da Vinci in Florence which has since disappeared.
This is the last picture I took of Anghiari and of my ride. Following Via Libbia into town, then up around a hairpin corner, you find a little gas station with this stunning view of Anghiari from above. There I asked an old man how to get back to Palazzo del Pero so that I could do La Foce back to Carlo’s place. He happily and enthusiastically obliged me after noticing my bike and explained in great detail the number of roundabouts to cross, that restaurant where I’m to make a right turn and the sections of road where I can “open’er up”. His directions were spot on. From Anghiari I took the same road that leads Monterchi then found 20kms of empty dual carriage-way before reaching Palazzo del Pero. From there, it was the La Foce again but this time in total darkness which was ass clenching.
This delta of Tuscany, Umbria and Marche was unforgettable. I urge any history buffs to check out Castiglion Fiorentino, Monterchi and Anghiari for a mini medieval tour. For those just passing through, take the SS73bis passed Urbania and just follow the road all the way out to the Adriatic Sea – you won’t be disappointed.
My route, below, was about 200kms or 4 hours long. It took me nearly 7 hours what with all the stopping.