San Casciano is located in an area known for producing good wine and quality cuisine in Tuscany. Chianti is an area characterized by traditional farms and wineries, but also enriched by numerous churches, parish churches, castles and medieval villages.
In terms of churches, check out the parish church of Santa Cecilia in Decimo, conveniently near the residential center, the Romanesque church of San Giovanni in Sugana, the church of San Pancrazio - a breathtaking example of Longobard-influenced Romanesque architecture - and the church of Santo Stefano a Campoli (from 903), near Mercatale Val di Pesa.
There’s as many spectacular villas as there are churches, so be sure to check out Villa i Collazzi and Villa Tattoli near the town of Cerbaia.
In Sant’Andrea in Percussina, head to Villa Bossi-Pucci, also known as l’Albergaccio, known for having hosted Niccolò Machiavelli during his exile. Also have a look around Villa Mangiacane, built by the Machiavelli family and, according to several studies, designed by Michelangelo Buonarroti with later additions by Giorgio Vasari.
You’ll also find impressive castles scattered around the region: add the castles of Bibbione, (built before the year 1000), Pergolato and Gabbiano, with their distinctive round towers and crenellated outside walls, to your list of things to see.
In La Collina, the Tomb of the Archer is well worth a visit. An Etruscan tomb dating back to the 7th century BC inside of which vases, lids and ivory plaques were found.
In terms of more contemporary works, have a look Mauro Staccioli’s sculptures in the hills, but it’s also worth heading a few minutes from San Casciano to see the fascinating and innovative Cantina Antinori, a production center and museum and in itself a work of art with its unique architecture. Among the artistic and historical works preserved inside is a letter by Giacomo Puccini, ceramics by Della Robbia and paintings by Lucio Fontana.