Castiglione della Pescaia is a small town nestled peacefully between the countryside of Maremma and the Tyrrhenian Sea, primarily known today as a tourist destination.
However, the typical Medieval market town overlooking the 'new' area of the town was once part of the Republic of Pisa. After a precious moment of respite as a free municipality in the late 14th century, it came under the rule of various regional lords. Then, in the 18th and 19th centuries, the region experienced a boom thanks to the opening of the port, followed by the railway of Maremma.
More chic than some coastal areas further north, but less exclusive than others further south, Castiglione stands out thanks to its small port and the boats that are moored there. It is an excellent gateway to 'authentic' Maremma.
Once you've visited the centre of Castiglione, you will find many villages in the surrounding areas which are definitely worth a trip: Scarlino, Massed Marittima, and Gavorrano. Going deeper into Maremma, you will come across small towns and villages displaying that Medieval aspect which makes up the charm of the region. Not to mention that the road is scattered with restaurants and agritourism establishments, which are perfect for an improvised stop to, for example, discover the local gastronomy.
Towards the north: following the sea, you will come across the headland of Punta Ala. Located just opposite the small, uninhabited Sparviero Island, the headland tapers off into the small port of the same name. This is a rather elegant seaside town that is especially striking for its surrounding landscapes. Although it isn't classified as a protected zone yet, it has been declared "of regional interest"; an official status which protects it from certain threats.
Towards the south: continuing along the sea, you will arrive at Monte Argentario and Oporto Ercole. This zone of protected nature affords particularly authentic landscapes. As the story goes, it is in Oporto Ercole that Caravvagio died in 1610; today, the small town is mostly known for being a luxurious and elegant tourist destination.
Traditional Festivals: the Balestro del Girifalco, a medieval tournament which is held in Massa Marittima twice a year: the fourth Sunday in May and the second Sunday in August.
The historical centre of Castiglione, which dominates the new town and the small port from its citadel.
In Castiglione: the 16th centuryChurch of San Giovanni Battista (Saint John the Baptist).
In Massed Marittima: the main monuments, like the Cathedral of San Cerbone (a Romanesque-style cathedral), the Palazzo dei Priori and the Palazzo del PodestÓ, can be found around the Piazza Garibaldi, in the heart of town.
InScarlino: the Rocca aldobrandesca or Castle of Scarlino, a fortress dating from the 10th century.
The tourist farms are often located on small hidden roads that are poorly signposted, and it is sometimes hard to find them, even if you have GPS. So just make sure to (1) stay calm, (2) have a good map of the region and (3) don't hesitate to ask passers-by for directions.
To explore Castiglione and its surrounding areas, you unfortunately need a car, especially if you want to go follow the marked itineraries.
Castiglione della Pescaia is a small seaside town, which means there are plenty of fish dishes to try, which are generally served with tomatoes of some form. However, it also serves as the gateway to Maremma, which is why you can also find game meat specialities here, such as wild boar or hare.
The mention of Maremma evokes the idea of Tuscany and, by analogy, "the fantastically wealthy food and wine culture". You will of course have the opportunity to purchase some olive oil, which you can buy from a large, popular manufacturer, an independent artisan, or even an organic producer. That's not to mention all the different flavours you will be able to find. As for wine, the choice is just as vast.