Exploring villages is an activity that in this part of Tuscany can offer great surprises: from a small town by the sea that for over a century has attracted artists and movie stars, to charming villages perched on hills with views of the sea and its islands. All of them are worth a visit, but here we present our favorites.
Montescudaio, a vantage point among olive groves and vineyards
Montescudaio is one of the most beautiful villages in Italy and is located less than 10 minutes by car from the hu Montescudaio village. To get there, you drive along a road surrounded by woods. After a few curves, the small town with red rooftops greets you, nestled among olive groves and vineyards—where the prized Montescudaio Doc wine is produced—with its narrow streets climbing steeply to the old castle that still dominates the town, encircled by imposing walls, some of which are up to 15 meters high. Catch your breath, walk along the quiet, well-maintained cobbled alleys, and reach the vantage point from where, on the clearest days, you can spot the profile of Corsica, beyond the islands of Gorgona and Capraia. If you're a wine connoisseur, the best and most fragrant time to visit the village is during the Wine Festival, which takes place on the first weekend of October.

Montescudaio
Casale Marittimo, Tuscany at its finest
Perhaps one of the most charming, lively, and well-preserved villages in this hilly stretch overlooking the coast, Casale Marittimo clings to a steep hill and is centered around its small square. In the summer, the best time to visit the village is at sunset. After a day by the sea, it will be a relief to enjoy the breeze during the aperitif hour: the central Piazza del Popolo is filled with cafes, and you'll have no shortage of choices. Before or after your well-deserved relaxation, take the time to wander through the village's streets, search for the remnants of the ancient castle hidden among the houses, the Clock Tower, and the countless scenic views of the countryside. Breathe it in—it's a beautiful moment. If you happen to be here on summer evenings, check the local event calendar and look out for the snail festival, where you can taste the traditional snail cacciucco.

Casale Marittimo
Castiglioncello, for lovers of beauty
A small district of Rosignano Marittimo located along the coast, Castiglioncello occupies the last stretch of the Livornese mountains. Once a small fishing village with ancient Etruscan origins, its peaceful yet elegant atmosphere attracted—and still attracts—lovers of beauty. It’s no coincidence that, towards the end of the 19th century, Castiglioncello was chosen as a favorite vacation spot for artists and intellectuals, particularly members of the Macchiaioli painting movement, and was nicknamed the "pearl of the Tyrrhenian Sea." The pine forest and the cliffs overlooking the sea around the village hide luxurious, inaccessible villas, and you may have seen this stretch of coastline in unforgettable scenes from the film Il Sorpasso, directed by Dino Risi and starring Vittorio Gassman and Jean-Louis Trintignant. But in Castiglioncello, you can also come for a walk by the sea along the Bay of Quercetano or under the pine trees, and especially to enjoy a bit of the social life and elegance—sometimes a bit old-fashioned—of this place, where the nightlife revolves around Piazza della Vittoria, a must-stop when passing through. So, stop by the legendary Caffè Ginori, a piece of 20th-century history, a symbol of La Dolce Vita. From the square, you can also access the public park that leads to the neo-Gothic Pasquini Castle, where cultural events and festivals are held in the summer.

Castiglioncello
Campiglia Marittima, Medieval views of the islands
A maze of uphill alleys, quiet little squares, and medieval glimpses: Campiglia Marittima may seem like a typical Tuscan village, but it's even more than that. It's a lively town that attracts visitors with its stunning views—a blue backdrop with the islands of the Tuscan Archipelago floating in the distance—and its history is written on the Palazzo Pretorio, adorned with coats of arms. This building was once the seat of the podestà sent by Florence to control the territory, and today it houses the Guarnieri Museum, which displays paintings and woodcuts by Carlo Guarnieri, a master of Italian woodcut art born in Campiglia, as well as a Mineral Museum, the first clue to another important history that defines this village: its mining heritage. From Piazza della Repubblica, you can also climb up to the fortress, the residence of the Della Gherardesca family. A special time to visit Campiglia is in mid-August when Apritiborgo, a lively street theater festival, transforms the streets and squares into small and original stages for performances.

Campiglia Marittima
Suvereto, passing through Sassetta
If you're planning to visit Suvereto, consider reaching it via Castagneto Carducci along the provincial road 329: it's probably one of the most beautiful routes in this area. You'll pass through rolling hills, green meadows, fairy-tale forests, isolated farmhouses, and villages forgotten by time. Before reaching Suvereto, you can make a stop in Sassetta for a quick break at the Art Caffè Bar Roma and take a stroll through this village nestled in the woods, where you'll encounter curious sculptures and art installations. Once you arrive at your destination, you'll realize that the beauty of the journey keeps building, as Suvereto is the most charming village in the Val di Cornia. Surrounded by an oak forest (from which it gets its name), the town embraces the ruins of the Aldobrandeschi Castle. Explore the village at a leisurely pace, then indulge in the pleasures of the table at I'Ciocio, a small temple of local cuisine.

Suvereto