San Casciano in Val di Pesa is the first town to greet you in northern Chianti, a gateway leading to the land of vine-covered hills. The territory of the town, whose center is a delightful village perched on a hill, is scattered with small fortresses, churches and hamlets waiting to be discovered in the winding bends of the Chianti hills.
Owned by the bishops of Florence since its foundation, San Casciano was annexed to the Republic of Florence in the 13th century and was later fortified as a stronghold to defend against the perils of the Siena countryside. Today you can still catch a glimpse of the impressive remains of the imposing city walls and medieval towers.
In town, don’t miss the San Casciano Museum: the two sacred and archeological art sections house works from across the municipality. Here you’ll find a remarkable reredos of the Archangel Michael and stories of his legend by Coppo di Marcovaldo, in addition to a striking Madonna with Child by Ambrogio Lorenzetti.
Among the many monuments, don’t miss the Collegiate Church of San Casciano and the Church of Misericordia (or Santa Maria al Prato), home to a stunning collection of artwork including a Crucifix by Simone Martini. The area is bursting with churches, a result of San Casciano’s important role in medieval times. Among these, check out the parish church of Santa Cecilia in Decimo, not far from 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. Last but not least, check out Villa Antinori in Cigliano and Villa Le Corti of the Corsini princes. You’ll also find some impressive castles scattered around the region: add the castles of Gabbiano, Bibbione Castle and Pergolato to your list of things to see.