After his retirement as a player in 1986, Chiarugi joined the Fiorentina youth team coaching staff. In his career, he served as Fiorentina's Caretaker manager three times. Late into the 1992–93 season, Chiarugi (jointly with Giancarlo Antognoni) replaced Aldo Agroppi with little fortune, as he did not manage to save them from relegation to Serie B after 54 consecutive seasons in the top flight. In February 2001, following the dismissal of Fatih Terim, Chiarugi was installed as caretaker coach for a single match, a 2–1 loss to Bari, before the appointment of Roberto Mancini. Following the departure of Ottavio Bianchi, Chiarugi was appointed again as caretaker coach during the dramatic 2001–02 season, which ended with relegation to Serie B and the successive club cancellation due to financial troubles, which ultimately led to Fiorentina's bankruptcy.