Castiglion Fiorentino

Set on a strategic hill between Arezzo and Cortona, Castiglion Fiorentino welcomes visitors with the unmistakable profile of its medieval tower. The village retains the intact charm of a border fortress, surrounded by thirteenth-century walls that enclose secret alleys, flower-filled courtyards and the surrounding countryside, the Val di Chio, where farming is still a millennia-old art.

Art and Culture

The focal point of the town's beauty is Piazza del Municipio, famous worldwide for the splendid Loggia of Vasari. Built in 1513, these arcades serve as a true cinematic viewpoint, framing the cultivated fields below. Behind the square rises the Cassero area, the oldest fortified core: here you can visit the Municipal Art Gallery, rich in Gothic sacred goldsmithing, and the Underground Archaeological Trail, which reveals the layers from the Etruscan period to the medieval era.

Nature and Outdoors

Getting lost in the Val di Chio is a rejuvenating experience. This side valley is a perfect mosaic of dry-stone walls, olive-grove terraces and small stone villages. Not to be missed is the path leading to the ancient Castle of Montecchio Vesponi, a perfectly preserved private fortress standing alone on a hill, once the home of the famous condottiero Giovanni Acuto.

Food and Wine

Val di Chio is famous for the production of a superior extra virgin olive oil, cold-pressed in the local olive mills. In the village shops, the olive oil enhances the flavor of Pecorino Toscano DOP, an excellent cheese tied to sheep farming and everyday cooking, and of scottiglia, an ancient stew of mixed meats from the peasant tradition.

Sport and Adventure

Lovers of cycling and trekking should not miss the Mulini della Val di Chio itinerary. It is an easy route of about ten kilometers that follows the banks of the streams to discover the old nineteenth-century water mills, perfect to walk or to rent an E-Bike to comfortably tackle the hilly gradients on guided tours along secondary roads.

Religious Routes

Castiglion Fiorentino is crossed by the evocative Cammino di San Francesco, a slow itinerary among medieval parish churches and hermitages. The spiritual place par excellence in the area is the Pieve di San Giuliano and the nearby Chiesa di San Francesco, a thirteenth-century Franciscan Gothic structure that houses a Renaissance cloister of rare elegance, ideal for a stop of silence and reflection.