San Gimignano to Arezzo and Anghiari: Private day trip

Thanks to its strategic position, Arezzo has been a thriving settlement from nearly 3000 years. Unfortunately, this also made it a target for Allied bombing during World War II, which destroyed large swaths of the city. Despite this, the city is still rich with historic monuments for visitors to enjoy. Visitors can stop by the 13th century Church of San Francesco, which houses the exceptional Early Renaissance ‘Legend of the True Cross’ fresco cycle by Piero della Francesca, or step into the 16th century Casa del Vasari, which is lavishly decorated by the owner himself. The gently sloping Piazza Grande is surrounded by historic buildings, such as the unique Chiesa di Santa Maria della Pieve, and the Grand Art Gallery, and hosts Italy’s most famous antique fair the first weekend of every month.

Overlooking the Tiber River, this charming hilltop village likely began as a Roman vineyard, as as evidenced by the wine cellar uncovered in the Palazzo Pretorio. Thanks to its strategic position and fortified walsl, the town played an important role in the Middle Ages, with the flat valley below setting the scene for the famous Battle of Anghiari in 1440, which was commemorated in Florence with a fresco by Leonardo da Vinci. Unfortunately, the painting deteriorated due to Da Vinci’s experimental technique, though Anghiari has a museum dedicated to the battle and the artwork. At its center, the Palazzo Taglieschi houses to the Museo Statale, which exhibits holds important art such as a colorful wooden Madonna by Jacopo della Quercia, and a sixteenth-century table organ.