Calamai studied at the Academy of Fine Arts in Florence under Pietro Benvenuti. The artist's peak period of activity can be dated between 1817 and 1836. During these years, he received several awards at the Academy exhibitions, and in 1824, he won the Pensionato in Rome; that same year, he also won the Curlandese Prize in Bologna. In the decade from 1825 to 1836, he produced his most significant works, which brought him considerable fame: Dante and Farinata, in which he shows an early interest in Romanticism; Galileo Visited by Milton; The Plague of Florence. Calamai was also a highly respected draughtsman. Since 1836 his activity slowed, perhaps because his disorderly life, which is mentioned by his contemporaries.