City Walls: Castiglione contains remains of two different city walls. The Pisans erected a first fortified perimeter in the 10th century, delimiting the village on the hill from the lower settlement. Over time, constant pirate attacks led inhabitants to move to higher ground, abandoning the area near the river. In the 15th century, the Aragonese (and later the Sienese) built new walls to delimit the village we see today (situated around the castle). The castle walls still preserve three entrance gates: San Giovanni, Madonna del Giglio and del Castello.
Castiglione Castle: this fortress is the village’s dominating structure. The original building dates to the 10th century when the Pisans first built a tower. In the 15th century, the Aragonese further enlarged the structure and turned it into a fortress, which was further modified by by Cosimo I de’ Medici and later, the Lorraine family. In the early 20th century the castle was entirely transformed to became a private residence, closing it off to visitors until today (it is still under private ownership).
Pineta di Tombolo: this coastal pine forest in located in the province of Grosseto and extends from Castiglione della Pescaia to the Padule della Trappola. The vast area stretches about 15 kilometers along the coastline, all within a protected nature area.