Main Route: Paganico - Sasso d'Ombrone - Poggi del Sasso - Montecucco - Cinigiano - Porrona - Montenero - Montegiovi - Montelaterone - Castel del Piano - Seggiano.

The itinerary passes through the most important Montecucco DOC wine-growing zones. Setting off from Paganico, a lively, modern town with an interesting four-gated wall dating from the fourth century ???, we reach the Monteverdi farm and then on to Sasso d'Ombrone, with its imposing bridge and medieval gate. We then climb up to Poggi del Sasso, a little rural town and centre of Montecucco wine production. This area is abundant in vineyards, cellars and wineries, but is also noteworthy for the beautiful castles at Vicarello and Colle Massari. A few kilometers from Poggi del Sasso is the Montecucco Farm which has lent its name to the eponymous DOC wine. This area, in front of Mount Amiata, is the heart of wine-growing activities. Numerous holiday farmhouses, traditional trattorie, and extensive wildlife make this area very rewarding from the hunting and culinary point of view. Nearby is the Porrona Castle, a stunning village whose image has been borrowed to promote DOC Montecucco wine. Montenero is the other DOC Montecucco "capital",and it houses the Museum of Wine and Vine. There are many cellars where wine, oil and other local products may be savoured.

During the summer in a park in Montenero an open-air wine bar is set up for the tasting of Montecucco wine. Also here one may visit the seventeenth century well and the town wall gate. Leaving Monyenero and proceeding towards Mount Amiata we arrive in the Montegiovi area - a veritable museum of viticulture, with its little groves of mixed olives and patches of vines. In fact a real vine museum is planned for the conservation of germoplasm and particularly autochthonous species of grapevine. Also to be admired is the centre of Montegiovi, where on the last Sunday of September a country fair, devoted to Bruschetta, is held. Montelaterone is the last village before Castel del Piano - the incredibly well-preserved centre is worth a visit.

Then Castel del Piano itself: it is one of the most important towns of Mount Amiata, and the visitor should seek out Palazzo Nericci, which is soon to be a museum dedicated to peasant culture, the Castiglionese Gate, Corso Nasini, the Monaci, Cantucci, Bruni, Alluigi and Cerboni Palaces, the Teatrino and the Loggia della Mercanzia. The trail finishes up in Seggiano, or rather a little further on - another area given over to vine and olive-growing. Here the Logge del Mercato and the historically important centre, with its cellars carved out of rocks, are worth seeing, as are the charming Potentino Castle and Daniel Spoerri's unusual "Garden of Art". One should also visit the Olivastra Seggianese olive-pressing works where the only single-variety Tuscan oil, denominated "Seggiano", is produced from the locally cultivated Amiata olive. The annual Oil Festival is held on the first Sunday of December.

Mini-itinerary: Monte Antico - Casenovole - Casal di Pari - Bagno di Petriolo

This trail is particularly rich in history, as the Castles of Monte Antico and Casenovole testify. We wind along a route not far from the River Ombrone, in an area once famous for wine-growing and which is today regaining it old splendor and vocation. The little towns of Pari and Casal di Pari, veritable rural gems, are a must, as is the charming spa of Petriolo, set in the Nature Reserve of Basso Merse. There are also numerous farm guesthouses and traditional restaurants, making this place rather special.

Mini-itinerary: Paganico - Civitella Marittima