Wedged between sea and mountains, Cinigiano in Maremma is a richly contradictory land which finds its most profound significance in the diversity of landscapes and atmospheres. The Municipality extends from the Riserva di Poggio all'Ombrone, where gentle hillsides climb from the plain and the river flows among white and flat stones, to the thick fir shadows of Mount Amiata overlooking villages, castles, farm houses and hamlets dotting the valley.

An ideal itinerary starts from the road which, after leaving behind Grosseto and heading to Istia d'Ombrone, continues on in the direction of Granaione. Upon reaching the Melecce torrent, which cuts a deep course inside the rock, one enters the less well-known inner area of the valley, and reaches Piantaverna, where the words "Ente Maremma" (the agency responsible for the land reclamation project that turned this region's malaria-infested swamps into farmland) are inscribed on the façade of the town's characteristic white houses. The road than proceeds through a pleasant landscape of vineyards surrounding Poggi del Sasso, a small rural village and the hub of Montecucco wine production. This is the major grape and wine production area, where wine enthusiasts can visit many local estates and cellars. A number of castles emerge from the vineyards, including Colle Massari, dating back to the sixteenths century, and Vicarello, already recorded in 1220 as Vico del Diplomatico di San Salvatore al Monte Amiata.

A little further on, one finds more castles, more tales of this land. Here is Castel Porrona, to this day one of the most typical and best-preserved Tuscan villages. Grape-harvesting season is the best time to visit. In September, the Feast of "capitone" (eel pickled in vinegar) is a reminder that Sasso d'Ombrone is indissolubly linked to the river that meanders, with its lazy and ever-changing bends, at the foot of the ruins of the fortress, of which only a few ruined walls remain. The river plain, well-suited for cereal growing and stock-farming, surrounds the village, built on a rocky outcrop.

In the Piani Rossi (red plains) area, named for the colour of the soil, stands the modern village of Santa Rita, a centre of industrial and artisan enterprise close to major highways. The Ombrone River and its Orcia tributary, mark the north-eastern border of the Municipality, as well as its lowest-altitude point. From here on, the hills begin to ruffle into clay calanques, and the Trisolla torrent leads us to Cinigiano. Here, in early October, the smell of freshly pressed grapes announces the beginning of the Grapes Festival and in the very heart of the town the ancient Contrade (boroughs) of Cassero, Molino and Salendo drape the streets with their respective colours.

At the end of a little climb, one reaches Monticello Amiata, with its famous chestnut trees. Beyond Monticello is Castiglioncello Bandini, a lofty castle built by the Aldobrandini noble family. Up there, on a firm and clear morning, those who look at the horizon discover a faraway glitter and island out that one would have never dreamed of being able to see. There, over the horizon, the sea of Maremma disappears.