On the city side of the hill behind Pitti Palace there is the wide garden of Boboli, done by will of Cosimo I de' Medici starting from 1549 and following the project by architect and sculptor Niccolò Pericoli called Il Tribolo; after him the building works were directed by Ammannati and then Buontalenti.The garden was intended to act as an appropriate scenery to the exclusive parties and governmental receptions by Medici's Court: it consists of a plentiful ensemble of greenery and architectural works.

The entrance is at the end of the inner court of Pitti Palace and consists of a large stairway leading to a wide square with the Fontana del Carciofo (Artichoke Fountain). In the center of the garden there is the amphitheatre, where were once played dramas and comedies in a classical manner for the Court's guests. During the XIX century, when was fully lost the dramatic function, it increased its scenographical function with the installation of a marble fountain belonging to the Roman Age and an Egyptian obelisk.

On the slope of the hill there is the stately boulevard of Viottolone, decorated with series of age-old pines and cypresses, which leads to the Piazzale dell'Isolotto (Islet Square), a wide open space with an small artificial lake, in whose center there is an islet with plenty of plants decorating the Ocean's Fountain, performed by Giambologna in 1576. From there start two paths: one to the Forte del Belvedere (Viewpoint Fortress), with a beautiful panorama over Florence; the other leads to the Casino del Cavaliere (Knight's House), which nowadays hosts the Museum of Porcelain, with a rich collection of porcelain and ceramics in the main factory of the times.

Going back down to the Pitti Palace from the other side there is the path leading to the Grotta Grande (Great Grotto), a rich and imposing complex of statues and fountains, mainly performed by Buontalenti, which alternate with suggestive calcareous natural formations and which was once animated by an infinite variety of water games.