Cortona and Lake Trasimeno

At 600 meters, Cortona rises above the Val di Chiana, its medieval walls tracing a skyline that predates Rome’s expansion. Inside the MAEC (founded 1727) you’ll find the famed Etruscan bronze chandelier and funerary stelae from nearby Camucia; in San Domenico, a panel by native son Luca Signorelli, and Baroque canvases by Pietro da Cortona in the Duomo. Then the scene shifts to Lake Trasimeno—128 square kilometers of shallow water and the site of Hannibal’s 217 BC ambush—where shoreline villages trade fishermen’s boats for trattoria terraces.

Your day runs smoothly from hotel pickup in Montepulciano, with a Mercedes at your disposal and a flexible pace while your driver handles routes and parking. Near Porta Colonia you’re dropped right at the old town, then it’s a 40-minute run along the SS71 to Castiglione del Lago for lunch by the water. Try tegamaccio, the local lake‑fish stew, add a short walk on the fortress ramparts or a boat hop to Isola Maggiore, and return via Valiano’s vineyards as the light softens.