Montaio: Castle, history and landscape

An Etruscan-Roman settlement, traces of fortifications and the Church of San Silvestro give Montaio several historical layers. A circular walk of about 11.5 kilometres passes through the village. On the slopes of Montaio-Grimoli, olive groves alternate with small vineyards. You can get to know Montaio through both its village and architectural history and its walking trails and landscape.

From settlement to fortified castle

The first documentary references to Montaio date from the 12th century. Towards the end of that century, the castle also exercised jurisdiction over the municipality of Cavriglia. Historically, it stood on a strategic link between the Valdarno and Siena—a connection that places Montaio in the region’s history but says nothing about present-day transport routes.

The fortified village was besieged and conquered by the Florentines in 1252. After the conquest, its walls were completely demolished. Following the village’s destruction, the castle was rebuilt and later shared the fate of the Republic of Florence. The earliest surviving statutes of the municipality of Montaio date from the late 14th century. Together, these facts tell of different phases: the medieval castle, the destruction of the fortifications and later forms of community life.

Castle, rings of walls and Romanesque arch

Montaio Castle is still clearly visible today. It stands at the top of a steep hill above Cavriglia. Fragments of two rings of walls can be seen on the slope; the former entrances to the castle can also be identified. Another architectural detail is the Romanesque arch that carries the road in Montaio. The castle and these architectural traces bring the history of the fortifications to life beyond the recorded dates.

San Silvestro and ecclesiastical history

Today, the Church of San Silvestro displays Neoclassical architecture in a style typical of the 19th century. Sections of the medieval walls that once surrounded the village are incorporated into its rear. The church thus brings together a later architectural form and older elements of the fortifications.

As early as 1299, San Silvestro was one of the churches under the authority of the Pieve di San Giovanni Battista in Cavriglia. An old hospital dedicated to Saint Paul also stood beside the church; it was mentioned as early as a pastoral visit in 1446. The Museo di arte sacra della Pieve di San Giovanni Battista di Cavriglia also displays objects from the churches of Montaio. The church’s history therefore extends beyond the building in Montaio to include the objects displayed there.

Circular walk and hillsides

The CAI circular route Anello Cavriglia–Montaio–Grimoli–Parco Fotovoltaico passes through Montaio. The loop is about 11.5 kilometres long and is described as easy to walk. If you include this route in your travel plans, check the current trail conditions before setting out, as they may change. The approximate length and circular nature of the route also give you a practical basis for planning your time, without specifying an exact walking time.

The slopes of Montaio-Grimoli are characterised by alternating olive groves and small vineyards. Together with the Romanesque arch and traces of the castle, they offer a different perspective on Montaio from the chronology of its siege and rebuilding. When planning your trip, you can therefore decide whether the historic buildings or the walk should play a greater role in your stay.

Discover more destinations: Montegonzi, Meleto, Castelnuovo dei Sabbioni

Return to the main travel overview: Cavriglia.