The origins of Certaldo, as shown by some archaeological finds in the area, date back to the Etruscan-Roman Era. Its name is derived from the Latin "cerrus alto" (or the Germanic "cerrus aldo") meaning "high plain covered with oaks" (trees). Its history has been documented since 1164 when Federico il Barbarossa conceded the territory to the Alberti Counts, who kept control until the late 13th century. It was then assigned to the Republic of Florence. In 1415 Certaldo became the seat of the Vicariate, and its importance was such that, in the Medici period, it was the most important political and judiciary centre of the Valdelsa.

The "Castello", the ancient village, inside generally well preserved city walls, is accessed by Porta Alberti, Porta al Sole and Porta al Rivellino. The "rivellino" or outpost, with its fortified walls represented an external defence to the village to dominate the underlying valley with the important Via Francigena running through it. The village can be reached by the ancient steep streets called Costa Alberti e Costa Vecchia, or by the more modern Via del Castello. The sight that meets the eyes is a strongly medieval example of town planning, although it was developed during the Renaissance, which culminates in the imposing Palazzo Pretorio at its peak. The facade, entrance hall and courtyard all bear the insignia of the different Vicars, including the marvellous glazed terracotta coats of arms created by the Della Robbia workshop.

The natural heritage of the territory of Certaldo, which includes areas of natural and geological interest, has been improved by the Commune’s initiatives to safeguard and conserve the environment, also for a correct use for sporting and recreational activities.

The programme "Dolce Campagna, Antiche Mura"(Gentle countryside, Ancient City Walls) has been geared towards natural and cultural excursions, with four itineraries for hill-walking, mountain bike and horse-riding, all joined together in a four-leafed clover design and connected by a large ring-shaped path (130 km), with the same number of itineraries in the surrounding communes and with a "halting place" in the Fiano locality which offers overnight and longer term accommodation.

The River Park has recently been created to follow the banks of the River Elsa, including an area from Gambassi Terme as far as Castelfiorentino. The Hill Park, equipped by the Presbytery has also been opened recently: a wonderful wooded area for excursions and picnics, also equipped with professional open-air gymnastic equipment.