Such an ancient territory naturally produces many prominent figures some of which pushed their fame beyond local borders while others quietly and deeply rooted their lives in Montespertoli.

Sidney Sonnino: journalist, mayor, deputy and minister in the second half of the XIX century, he paid great attention to the Southern Question and dealt with the problems of the peasant class; Amedeo Bassi: an opera tenor to whom a museum in Piazza Machiavelli is dedicated; Don Lorenzo Milani: priest, writer, teacher, Catholic educator and charismatic intellectual figure; Domenico Pugliani: painter and mayor of Montespertoli in 1646; Francesco Guicciardini: writer, historian and politician, almost a monument to the XVI century Italian intellectual class and in particular to the Tuscan-Florentine school of philosophical historians; Cino Cinelli: professional cyclist between 1937 and 1944 who won 3 stages of Giro d’Italia, Giro di Lombardia and the Milan-Sanremo.