The region around Castiglione della Pescaia was first inhabited by the ancient Umbrians and Etruscans, then later by the Romans, who built the first fortifications on the hill overlooking the coast and the inland lake, which was rich in fish and salt. In the Middle Ages it was attacked repeatedly by pirates, recovered under the protection of Pisa and the Papacy, and became an independent commune in the 13th century, when it suffered many years of disease and hardship before eventually becoming part of the Dukedom of Tuscany, and eventually the province of Grosseto.

Today it is a famed tourist destination. The beach is pristine and considered one of the best in Italy, the town’s natural surroundings – the coastline, marshes, and woodlands – are meticulously preserved nature reserves, and the old city on the hill below the striking 12th century medieval fortress is gorgeous.