Penna San Giovanni is a comune (municipality) in the Province of Macerata in the Italian region Marche, located about 60 kilometres (37 mi) south of Ancona and about 30 kilometres (19 mi) south of Macerata.

Penna San Giovanni borders the following municipalities: Amandola, Falerone, Gualdo, Monte San Martino, Sant'Angelo in Pontano, Servigliano.

Penna is an ancient hill top town.

There are half a dozen churches and a small early 18th-century theatre, Teatro Flora.

In the summer the municipality organizes events on numerous evenings, including the Festa della Polenta and Otto Giorni Di Un Linguaggio Volgare.