Macchiaioli painters who dedicated time to Castiglioncello included Giovanni Fattori, Silvestro Lega and Telemaco Signorini, among others.
From 1843 to 1847 he attended the Accademia di Belle Arti, Florence, studying drawing under Benedetto Servolini (1805–79) and Tommaso Gazzarini (1790–1853), then studying painting, briefly, under Giuseppe Bezzuoli.
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As a Garibaldian volunteer, Lega participated in the military campaigns for Italian independence (1848–9) before resuming his training, this time under Antonio Ciseri, completing his first large-scale painting, Doubting Thomas (1850; Modigliana, Osp. Civ.).
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Afterwards he moved to Florence where, at the Caffè Michelangiolo, he met Giovanni Fattori, Silvestro Lega, and the rest of the artists who would soon be dubbed the Macchiaioli.