Originally designed for the Medici, it represents one of the first and most important examples of the Italian garden, which later served as inspiration for many European courts.

The mid-16th-century garden style, as it was developed here, incorporated longer axial developments, wide gravel avenues, a considerable "built" element of stone, the lavish employment of statuary and fountains, and a proliferation of detail, coordinated in semi-private and public spaces that were informed by classical accents: grottos, nympheums, garden temples and the like.

[1] The primary axis, centered on the rear façade of the palace, rises on Boboli Hill from a deep amphitheater;[5] its shape resembles half of a classical hippodrome or racecourse.

At the center of the amphitheater and rather dwarfed by its position is the Ancient Egyptian Boboli obelisk[1] brought from the Villa Medici at Rome.

Initially formed by clipped edges and greens, it was later formalized by rebuilding in stone decorated with statues based on Roman myths such as the Fountain of the Ocean (sculpted by Giambologna, later transferred to another location within the same garden).

Decorated internally and externally with stalactites and originally equipped with waterworks and luxuriant vegetation, the grotto is divided into three main sections.

The first one was frescoed to create the illusion of a natural grotto, a refuge that allows shepherds to protect themselves from wild animals; it originally housed The Prisoners of Michelangelo (now replaced by copies), statues that were first intended for the tomb of the Pope Julius II.

[6] The Fontana del Bacchino is a 1560 sculptural work by Valerio Cioli (1529–1599) featuring a statue in the likeness of the famed dwarf buffoon from the court of Cosimo I de' Medici, Grand Duke of Tuscany, Nano Morgante modeled after Bacchus and riding a tortoise.