Grand Tour of Tuscany by bike - from Siena toward Camaldoli and Arezzo

The Grand Tour of Tuscany by bike - from Siena toward Camaldoli and Arezzo is one of three major itineraries designed to allow the cyclo-traveler to touch on all the major locations of Tuscany. Base of departure is Siena, a jewel city located in the center of Tuscany and the point of contact for the three itineraries. Each is about seven days long, which can be increased as desired to stop and better visit the most important cities. All to be able to say, with full knowledge of the facts, that you have truly visited Tuscany.

Leaving Siena we head east, following the route of the Eroica, the route on dirt tracks that winds through historic farms, vineyards and castles. After passing Montaperti, the site of the famous battle between Guelphs and Ghibellines in 1260, we reach Gaiole in Chianti, an ideal place for a food and wine stop. We leave the Eroica and Chianti to descend toward the Arno Valley. A few kilometers later, on the left is the detour to Badia a Coltibuono, an ancient Vallombrosian abbey now converted into a charming hotel.

When we reach Montevarchi, we cross the river and begin to climb up the opposite side, up to Loro Ciuffenna, a town of Etruscan origin built along the gorge of the stream of the same name.

Also not to be missed is the short detour for the Parish Church of San Pietro in Gropina, one of the highest examples of Romanesque architecture in Tuscany.

We continue north along the ancient road known as the Setteponti, along which we will encounter medieval villages and thousand-year-old parish churches.

After Reggello, the road starts to climb, beginning to enter the high Apennines. The landscape changes and large wooded areas begin; not surprisingly, our next half will be the abbey of Vallombrosa, a place of peace, serenity and coolness, already over a thousand meters above sea level.

We descend again toward the Arno River, which we cross again at the beginning of its long bend around Pratomagno. Before the final descent we have a visit to another wonderful example of Romanesque architecture, the parish church of Romena. With a left turn after the parish church, we also visit the castle of Romena, which gave shelter to Dante during his exile.

Descending to Pratovecchio we cross the river and begin the ascent to the hermitage of Camaldoli, another place where nature and silence interpenetrate perfectly with sacred architecture.

We continue along a beautiful high-altitude, partly unpaved, path that will take us to the Fangacci Pass at an altitude of 1274 m, the “Coppi peak” of the tour.

We descend toward Badia Prataglia to begin the last real climb of the whole tour, 500 m of elevation gain to overcome in 8 km to reach the sanctuary of La Verna, set on a rocky spur nestled in the woods, one of St. Francis’ most beloved places, where he received the miracle of the stigmata.

We continue to descend, this time toward the valley of the Tiber. The first village we come across is Caprese Michelangelo, the place of birth of Buonarroti, with his home turned into a museum.

Next town, Anghiari, one of the most beautiful villages in Italy. Below the village is the plain where another important battle took place, fought in 1440 between Florence and the Papal States. At the end of the very straight road that cuts through the plain (which we will avoid by choosing smaller, less busy roads) is Sansepolcro, the birthplace of another Renaissance giant, Piero della Francesca. In the town’s museum two of his most important works: The Resurrection and the Polyptych of the Misericordia.

We return to cross the plain, this time further south, to reach Monterchi, a small medieval village that holds another very important work by Piero della Francesca: the Madonna del Parto.

Next stop is Arezzo, which we reach along the old road, with little traffic, that snakes alongside the new state highway.

Arezzo certainly deserves a one-day-stop to admire all its beauties, starting with the very unique Piazza Grande.

We descend toward the Arno plain to take the cycle path of the Reclamation canal, which, pedaling through green fields and away from traffic, will take us first to Cortona, another village among the most beautiful and rich in treasures, reachable by a detour on the left, and then Montepulciano, which we reach by exiting the cycle path at Valiano and turning right.

After a visit to yet another wonderful village, we take a beautiful unpaved road (with a couple of hard rips, avoidable by using state road 146) that will take us first to Monticchiello, a small but delightful stone village perfectly preserved, and finally to Pienza, the ideal city of Pope Pius II Piccolomini, now a UNESCO site.

From Pienza we descend to Bagno Vignoni, another iconic place in Tuscany, with its large thermal pool that fills the square of the town. From here you can choose whether to continue along the Via Cassia (as indicated in the trail) or take the Via Francigena northward (the initial stretch after Bagno Vignoni has some very hard gravel climbs: recommended only for technically experienced and trained cyclists) to reach the villages of San Quirico d’Orcia, Buonconvento, Monteroni d’Arbia and finally Siena, our arrival point.

See also:

Grand Tour of Tuscany by bike - from Siena toward Pisa and Florence.

Grand Tour of Tuscany by bike - from Siena toward Pitigliano and Massa Marittima.