Along the road leading to Monte Amiata, still within the territory of Cinigiano, one finds the ancient village of Monticello Amiata.
The village was originally dominated by Monte Pinzutolo and is situated on a high hill, surrounded by a striking chestnut tree wood, and overlooks the valley of the Ombrone River. The walls enclosing the castle have retained their elliptical shape and are still visible, although many homes have been built over them. In addition, three protruding towers and two gateways are still preserved: the Monticelli gate and the gate of San Francesco.
The Parish church San Michele Arcangelo, looms over the village buildings and the colourful houses, separated by narrow alleys. The church of the patron saint of Monticello Amiata, stands in the centre of the village and preserves a superb painting La Madonna col Bambino by the Sienese artist Bartolomeo Neroni, a student of Sodoma, one of the most well known artists of 16th-century Italy.
On the outskirts of the town rises the church of Madonna di Val di Prata (1218), an ancient Marian sanctuary surrounded by a lovely park, in which are kept important works of art such as the altar-piece (1691) attributed to Nicola Nasini.

In Ripe the Cappella della Madonna del Lampino.

Casa Museo is a small ethnographic museum located in an old oilmill. The exhibition reveals many aspects of daily life, economy and folklore of the 18th and 19th centuries through a series of items, tools and reconstructions of domestic environments. The oil press with its huge millstone and the tools for chestnut processing are particularly interesting.

www.museidimaremma.it | Casa Museo
The Museums of Maremma | Monticello Amiata - Museum House

Do not miss the Festa della Castagna and the Festa dell'Olio: Monticello dedicates the second Sunday of October to the chestnut harvest and the last Sunday of November to the new olive oil.

In the surroundings of Cinigiano we also recommend a visit to the amazing Castle of Porrona, a perfectly preserved hamlet on the top of a hill with a fantastic view. The Castle of Colle Massari and the Castle of Vicarello are also worth a visit.
Castel Porrona belonged, between 1385 and 1894, to two large families of the Siena nobility, the Piccolomini and the Tolomei, and represents even today one of the most typical and best conserved villages one can find in Tuscany, offering a fascinating view over the surrounding valleys.
The Pieve di San Donato in Porrona is a simple but impressive church in Romanesque style, with a single nave with transept and apse. Inside San Nicola in trono con angeli e donatori attributed to Giovanni di Marco said "da Ponte; and a Madonna con Bambino by Girolamo di Benvenuto from the beginning of the sixteenth century.
The Chiesa della Madonna delle Grazie was built during the seventeenth century outside the walls of Porrona, and represents the typical stylistic elements of rural chapels.

In the area of Poggi del Sasso there is the Castle of Vicarello, which in the 13th Century was part of the holdings of Siena with the name of Vico. In 1438 the castle, now fallen into ruin, was bought by a noble of Castello del Cotone (which rises a little to the North of Scansano), who, in order to reconstruct it and bring it to its initial importance, obtained the privilege from the Republic of Siena of not paying any tax. The interior of the castle, in an L-shape around a courtyard that is entered by a gateway with a round arch, cannot currently be visited, given that it is private property.

The third castle in the Commune of Cinigiano is Colle Massari, which was originally recorded by the name of Colle Sabbatini and is on the border with the Commune of Campagnatico. The first owners were the monks of the Abbey of San Galgano, and then in 1278 two thirds of it passed to the Republic of Siena. In 1355 the part that was still the property of the monks of San Galgano was ceded to Guido of Castello del Cotone. It presents itself as a fortified farm, constituted by buildings that are developed in a U-shape around a rectangular-shaped central courtyard, and in the corners of the perimetral wall there are placed round towers with a trapezoidal base.
Today's Colle Massari, owned by sister and brother, Maria Iris Bertarelli and Claudio Tipa. Colle Massari was established in 1998 and is part of the Montecucco DOC in Alta Maremma, among the Docg Brunello di Montalcino DOCG and Morellino di Scansano DOC.
The estate covers around 350 hectares, including 82 hectares of vineyards, 22 hectares of olive groves, 50 hectares of sowable land and the remaining part woodlands and is surrounded by state-owned woodlands of approximately 1200 hectares.