Toiano: Historic Buildings and Green Hills

Toiano combines historic buildings with green hills and scattered, well-restored farmhouses. The Palazzaccio di Toiano, Castello Poggiarello, and Villa Chigi showcase different architectural forms and historical periods. There is also an almost entirely traffic-free circular route in the area between Caldana and Toiano. This gives you both cultural and rural themes to consider when planning your trip, as well as a specific cycling option.

Historic Buildings and Their Historical Periods

The Palazzaccio di Toiano has been documented since the 15th century, although some of its structural elements are much older. The complex includes a very tall stone tower with a sloping base, lower buildings, and sections of wall enclosing an inner courtyard. A large square portico completes the ensemble: a sturdy brick pillar supports it in the center, and the portico opens onto four brick cross vaults. The tower, enclosed courtyard, and architecture defined by the pillar and vaults represent different forms within the same complex. If you look at historic buildings through their design, the tower base and the vaults offer specific details to observe.

Castello Poggiarello has a different history. The fortress was built to defend the surrounding land and store the harvest, but was later converted into an aristocratic residence. Its surviving architectural features include a crenellated tower with a sloping base, a lower building section that is also crenellated, and several loopholes. Together, these features let you consider the transformation from the original fortress to an aristocratic residence alongside elements of its architectural design. In the garden of the Castello stands a chapel dedicated to Saint Augustine, built in 1558. The Castello is on the road connecting Caldana with San Giusto a Balli.

Villa Chigi in Toiano was built in the 17th century. Inside, it preserves frescoes dating from 1707. The construction date and the fresco date are two distinct historical reference points: the first refers to the villa, the second to the paintings inside. Thus, alongside the architectural history, the dated frescoes offer a specific artistic point of interest.

Hilly Landscape and Townscape

Toiano’s character is shaped by green hills and a landscape that seems unchanged over time. Well-restored farmhouses are scattered throughout the area. This combination of rolling hills and dispersed buildings draws the eye beyond the individual structures to the wider townscape. If you do not want to plan your trip around just one historic building, the landscape offers another way to experience Toiano’s character.

Villa di Toiano lies on the border between the Municipality of Siena and the Municipality of Sovicille and belongs to Sovicille. Its location on the municipal border and its municipal affiliation are therefore clearly distinct.

Tasting and Cycling Route

As of August 29, 2026, the Fattoria Poggiarello website listed an option to book tastings at the estate in Poggiarello di Toiano. If you are planning a tasting, check the current booking information.

The circular route “In bicicletta tra pievi, ville e castelli” (By Bicycle Among Parish Churches, Villas, and Castles) runs through the area between Caldana and Toiano and is almost entirely traffic-free. It connects San Giusto a Balli, Poggiarello, and Toiano. This gives you a separate way to visit these places as part of a cycling route; the buildings and local history offer a different focus. Check current road conditions before setting out.

Discover more destinations: Scrofiano, Castellina In Chianti, Badiaccia A Montemuro, Megognano, Montegabbro, Vagliagli, Colle Di Val D'elsa, Torri.

For the broader travel overview: Siena.