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

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

We start symbolically from Piazza del Campo, in Siena, to connect with the tracks of Le vie del bike project, the great itinerary that crosses Italy from north to south, and Eroica, the route of dirt roads. At km 44 we will cross SP 44 and meet Buonconvento, the quaint village on the Via Francigena, two kilometers away on our left.

Our route turns right, but if you want to take a break the detour might be a good opportunity. The next stop, Montalcino, is 20 km from the fork, and is probably the best place to stop for the night. Of course, in addition to visiting the beautiful medieval village and castle, you cannot miss a tasting of Brunello, the wine for which the town is known worldwide. In the morning, we set off again toward the Abbey of Sant’Antimo, one of the most beautiful Romanesque churches in Tuscany, also for its isolated location among the fields; a place of silence and beauty full of charm.

We begin to approach the lord of these lands; Mount Amiata, the ancient volcano now nestled in the woods that we will bypass by heading toward Campiglia d’Orcia, a village topped by the remains of the ancient fortress from where we can enjoy a superb panorama.

The next village will be Bagni San Filippo, where we can relax in one of the warm pools at the foot of the limestone concretion known as the “White Whale”.

One last effort and here we are in Radicofani, elevation 787m, the highest on the entire tour. The village is certainly worth a thorough stop, especially the imposing fortress of Ghino di Tacco, which dominates the village and all the surrounding territories.

We pick up from here the track of the Via Francigena, which we will follow until it bends left to enter Lazio. Instead, we will continue on to three towns of Etruscan origin and still medieval in imprint, decidedly very special. The first is Sorano, a town “carved” in tuff, with intricate urban planning and breathtaking views. The second is Sovana, smaller and more linear but intact in its beauty, rich in masterpieces, such as the Romanesque co-cathedral of San Pietro or the church of Santa Maria Maggiore. The third is Pitigliano, also rich in history and monuments and with an unmistakable skyline; it seems to rise directly from the tuff cliff on which it is built.

We begin our descent toward the sea; we pass the two beautiful villages of Manciano and Capalbio, until we reach Capalbio scalo, at the height of Burano Lake, a WWF oasis and the first place to take a swim in the Tyrrhenian Sea.

We begin the ascent northward, taking advantage of the track of the way of the Tuscan Coast, until we reach Orbetello, which we will reach with a detour to visit the fishing village and enjoy the spectacle of the flamingos in the lagoon.

If you don’t have the time constraints and enjoy the sea, devoting a couple of days to exploring the Argentario, perhaps with a foray to Giglio Island or the lonely Giannutri, could be a very fulfilling option.

Having resumed our track, we move away from the sea until we reach Grosseto, then return to the sea at Marina di Grosseto and then Castiglione della Pescaia, where we can take our last swim before turning back inland. We now follow the trail of the Grand Tour of the Maremma to reach Massa Marittima, also to be counted among the most beautiful towns in the region. Don’t miss the splendid cathedral of San Cerbone.

After Massa, it can be said that the return to Siena begins, but not before making the last unmissable stop on the tour, which is the Abbey of San Galgano, the open-air church used, due to its uniqueness, as a set for many films. Nearby is also the hermitage of Monte Siepi, with its mysterious sword in the rock.

Thirty-five more kilometers of Tuscany, among dirt roads, minor roads and small villages, and here we are back in the city of the Palio.

See also:

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

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