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If you prefer a seaside resort that is convenient and easy to reach, choose Follonica ; if you mainly want an old town with more historical charm, opt for Castiglione della Pescaia. In Follonica, you have a long sandy beach, beach establishments and also free sections, as well as a train station in town: it's simpler if you come by train. In return, the center is less picturesque and the atmosphere is that of a fairly sprawling seaside town, mainly geared toward summer vacations.
Castiglione della Pescaia has the advantage of its hilltop medieval center and a more distinctive setting, but it has no train station: you have to reach the town by bus from Follonica or Grosseto. The two are close, about 24 km and 30 minutes by car outside of traffic slowdowns; so you can stay in Follonica and visit Castiglione on a day trip. In the height of summer, expect bigger crowds and less smooth traffic along the coast. My choice: Follonica if you don't have a car or want a simple seaside stay; Castiglione if the setting of the old town matters more than ease of getting around.
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