The Viale dei Cipressi is now one of the symbolic landmarks of Tuscany, but its origins date back to a carefully planned landscape and territorial representation project commissioned by the Della Gherardesca family. This nearly five-kilometre-long straight road, flanked by over 2,540 cypress trees and set within a landscape of olive groves, vineyards, and cultivated fields, was created in the first half of the 19th century.
Its construction is attributed to Count Guido Alberto della Gherardesca, a key figure in the development of the Bolgheri area. The count promoted land reclamation, agricultural reforms, and infrastructure improvements, helping to make the Bolgheri landscape known and appreciated beyond local boundaries, with a vision that recognised its symbolic and representative value.
The road runs along the Bolgherese Provincial Road, starting near the hamlet of San Guido, and directly connects the ancient Via Aurelia (now a state highway) to the 13th-century Castle of Bolgheri. It is the only direct and scenic access to the village and has always served as a kind of “gateway” to the surrounding hilly landscape. The view is dominated by a perfectly aligned double row of cypresses, regularly pruned to maintain their slender shape.
At the start of the avenue stands the Oratory of San Guido, a small church built in 1703 by the Della Gherardesca family and dedicated to Saint Guido, bishop of Acqui and ancestor of the lineage. The building reflects the rural religious architecture of early 18th-century Tuscany. It served not only as a place of worship for the estate but also as a symbol of identity. Saint Guido was considered the family’s protector, and the oratory visually reaffirmed their connection to the land.
The oratory’s current appearance has undergone several restorations. In front of the building stands the obelisk dedicated to Giosuè Carducci, erected in 1908 to mark the centenary of his birth.
Giosuè Carducci, awarded the Nobel Prize in Literature in 1906, spent part of his childhood in Bolgheri, where his father Michele worked as a physician. His poem Davanti San Guido (1874) played a decisive role in making the Viale famous. In the famous lines
“I cipressi che a Bólgheri alti e schietti /
van da San Guido in duplice filar”
the poet transformed the avenue into a metaphor for time, homeland, and family memory. From that moment, the Viale became not just a physical space but a cultural and literary symbol.
In 1954, the Viale dei Cipressi was paved. Although there is no official date for its formal recognition, over time it has been included among the historical and artistic heritage protected by the Italian Superintendency and is now regarded as a national monument.
Today, the Viale dei Cipressi is not only a distinctive feature of the Tuscan landscape but also a tangible testament to the agricultural, cultural, and familial history of Bolgheri.
