The charming town is divided into two parts, the ancient upper being called Certaldo Alto and the more modern lower Certaldo Basso.
It is famous for being home to the family of poet and author Giovanni Boccaccio, who died there and was buried in its soil in 1375.
The town is also renowned for its Mercantia, an annual street art festival which blurs the line between reality and fantasy.
The four-day party showcases numerous street performers from across Italy, Europe and even the Americas.
This year’s festival is currently underway, starting on Tuesday and running until Sunday.
The event comes to life in Certaldo Alto, which has limited car access, for use by residents only.
When visitors arrive, they can park outside the walls or in the lower part and head up to Certaldo Alto by the Certaldo funicular, which operates every 15 minutes.
Within the old town’s walls, there will be dozens of performers lining its streets and filling its courtyards.
Stages host clowns and comedians, jugglers and fortune tellers, contortionists and acrobats, puppeteers and ventriloquists, magicians and illusionists, fire-eaters and dancers, actors and street musicians.
The enchanting scenery will transport visitors to another place and time, and everyone who enters this world will be swept away by its magical atmosphere.
The event encourages the active participation of its myriad spectators, who are invited to get involved spontaneously as assistants or protagonists in performances.
While the magic unfolds in the ancient upper part of the town, Certaldo Basso also comes alive during the festival, housing street stalls selling hand-made jewellery, clothing, masks, hats, books, herbal remedies and beauty products, hand-crafted leatherware and shoes, and a wide range of other arts and crafts.
And what would an Italian festival be without an offering of delicious food and wine?
Visitors to Mercantia can expect to indulge in traditional Tuscan fare, washed down with a glass of Chianti.