In fact, now there are no elements that can, so to speak, backdate the frequentation of this portion of the territory. The remains of the Paduline settlement, dating from the 1st century B.C. to the 6th century A.D., offer a glimpse of what Roman Castiglione may have been. Some of the most significant artifacts from the Paduline site are now at the Maremma Museum of Archaeology and Art.
The castle is first mentioned in 1163, although a reference to a concession of the piscaria owned by theabbey of Sant'Antimo appears as early as 813. The original part of the castle, consisting of an east tower with a scarp base, dates back to the first Pisan fortification of the 11th century. The present layout, with the connecting walls between the towers, is the result of an expansion in the 14th century.

From the castle, once you pass through the gate facing the sea, you can admire the entire coastal strip located to the west.
Castiglione della Pescaia, however, is not only sea and beach. Ximenes' "red" house, located inside the Diaccia Botrona Natural Reservoir, or what remains of the ancient lake Prile, represents the symbolic building of the man-environment relationship in Maremma. The structure, the lower part of which was characterized by the presence of cataracts, built in 1768 according to a project by Leonardo Ximenes was part of the hydraulic structures built for the drainage of the then Castiglione marshland wanted by Pietro Leopoldo of Lorraine. Today, the building houses the Diaccia Botrona Multimedia Museum. The museum allows visitors to observe from a privileged vantage point and, without disturbing the ecosystem of the reserve, on the fauna and flora that dwell in this lake environment.
For lovers of Etruscan civilization, nearby Vetulonia is a must-see destination. In fact, until the 19th century the village was known as "Colonna." It was physician Isidoro Falchi, an archaeology enthusiast, who discovered its true origins. The museum dedicated to him, located in Vatluna Square, holds artifacts from the necropolises located in the area and from urban neighborhoods. Poggiarello Renzetti, on the entrance road to the town, is one of the most archaeologically relevant areas.