Montemassi, Roccatederighi and Roccastrada — Ring tour

Embark on a difficult touring bicycle adventure through the heart of Tuscany with the Montemassi, Roccatederighi and Roccastrada — Ring tour. This 20.5-mile (33.0 km) route challenges you with a significant 2017 feet (615 metres) of elevation gain, taking approximately 2 hours and 17 minutes to complete. You will cycle through rolling Tuscan hills, Maremma plains, and wooded areas, passing picturesque olive groves and vineyards, all while enjoying panoramic views across the Maremman plain and towards historic villages like Montemassi with its castle.

Given the route's difficult rating and varied terrain, including potentially unpaved sections with stones and pebbles, ensure you have a good level of fitness and a suitable touring bicycle. The demanding ascents, particularly towards Montemassi, require preparation. Plan your ride to make the most of the scenic vistas, which can extend to Siena, the Metalliferous Hills, the sea, and even the islands of Giglio, Elba, and Corsica on clear days.

This ring tour is notable for connecting three charming medieval villages: Montemassi, Roccatederighi, and Roccastrada. Roccatederighi, perched on a hilltop, offers particularly broad panoramas. The diverse landscape, combining ancient villages with untouched nature, including oak, chestnut, and beech woods, makes this a truly engaging cycling experience in the province of Grosseto.