From a cyclists' point of view, several stretches of the 366 km route are difficult. The route can be travelled clockwise from Massa Marittima: cycle toward Siena along the provincial road no.162. In Pian di Mucini, turn right and pedal uphill for about 6km and go downhill toward the bridge in the direction of the hamlet of Prata.
Cross the provincial road #54, and continue toward Tatti, and then Sassofortino and Roccastrada.
Once you've reached Paganica (at 56 km), continue to reach the Grosseto-Fano highway (in the direction of Grosseto) until the Montorsaio crossroads. Take the overhead bridge that crosses the highway and continue uphill to Campagnatico.
Go to Granaione and climb up to the mountain plains of Monte Amiata. After 11km continue to climb on the Sp 7 highway “Cinigianese” and Arcidosso. Once you reach the Passo di Aiole (cat 115km) take the Sp 6 highway “del Monte Amiata” that goes downhill to Santa Fiora (at 120km). Sorano and Pitigliano are the towns that are the further away from the departure point so from here turn back towards the coast, passing through Manciano (at 187km) and Marsiliana.
From Magliano in Toscana (at 228km) continue on the Sp 160 highway until Scansano (at 247km), passing through Pereta: the road goes uphill, giving cyclists a fantastic view of the Maremma hills.
Once leaving “Scansanese” go downhill toward the Montiano crossroads. From ere you can reach the SS 1 Aurelia highway that you can cross. Grosseto is located at the 280km of the Gran Tour della Maremma. Continue toward the coast to Marina di Grosseto.
Just under the train bridge is where you'll find the route toward the Marina; across this, on the left, is the cycle path, which after 7km, leads to Castiglione della Pescaia. From here, return to Marina di Massa, passing through the towns of Grilli, Ribolla and Capanne.