The Gaiole in Chianti castles trail winds its way along the SS 408 road, the old Chianti road that runs parallel to the Massellone stream and partly beside the Arbia river. It’s a hilly route into the surrounding countryside.
Steep hills, oak forests, olive groves and remote vineyards distinguish the area. It was populated in Etruscan times, as testified by the Tomb of Castellina, and later by a Roman presence, as shown by the remains of a second to third century AD burial ground. Churches were erected here in the Middle Ages, landowners settled in the castles and wealthy merchant families had villas built, turning the land into large farms.
Being bored isn’t an option here with the myriad footpaths, horse riding trails and bike paths as routes wind up and down the hills to reveal the local scenery and abundance of history.