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Arezzo is a beautiful town that sits atop a hill at the crossroads of four valleys - Val Tiberina, Casentino, Valdarno and Valdichiana. The 'Man of the El' was discovered here and found to date back to the Paleolithic era. In the 9th century BC, it became the Etruscan Arretium and rapidly turned into one of the most important cities in Tuscany, due to its strategic position along the Via Cassia. Today it is one of the wealthiest cities in Tuscany. Even though the Medieval center was destroyed during World War II, Arezzo has plenty of remaining monuments, churches, and museums. The Church of San Francesco is probably the most famous, with the incredible Early Renaissance fresco by Piero della Francesca depicting the Legend of the True Cross. You should then head uphill to the Medicean Fortress, visit the Cathedral dedicated to San Donato, then back down to the Roman Amphitheater and the Church of San Domenico with the wooden Crucifix by Cimabue.