Castiglione della Pescaia on the coast west of Grosseto north of Capalbio has been settled since prehistoric times. The nearby settlement of Vetulonia was one of the twelve member cities of the Etruscan League, and Catiglione was a major Roman town, with a port, villas, palaces, and a consular road.

The Roman villa of the Paduline on the right bank of the modern town is part of a much larger archaeological site, and was a luxurious complex of buildings with beautiful mosaics, frescos, artworks and sculptures, and annexes with private baths. The modern Castiglione is a charming seaside town with fantastic beaches, cool cafes, and great seafood restaurants.