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This town is situated on a gentle hill overlooking the plains, the sea, the Argento coast and the lagoon at Orbetello. Built near the Etruscan town of Heba, it was an important city with the end of the Marsilian era in the 6th century B.C. Ruled by the Aldobrandeschi, occupied by the king of Naples in his fight against the empire, it was then given to the Pannocchieschi family and in 1345 became part of Siena’s dominion. Siena then proceeded to build the Cassero and restore the city walls. The gateways to the town are known as Porta Nuova, the 14th century Porta di San Giovanni and Porta di San Martino with its Romanesque church of the same name.
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Ruled by the Aldobrandeschis, Manciano was conquered by Orvieto and by Siena, then returned to the Orsini family, supported by the Duke of Milan allied with the church in the late 15th century, passing then under the protection of the Senate of Venice. The town is situated on top of a hill and protected by walls, with a maze of picturesque narrow streets. The houses still bear many of the original features of typical medieval dwellings. The Rocca (fortress), set on the highest point, was built by Siena in 1424.
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 This is one of the most interesting and significant historic and artistic towns of the Tuscan Maremma. Still partially enclosed by the original medieval walls with various gateways leading into the old centre, this town contains some of the most interesting historic works in Tuscany. Piazza Garibaldi, the main square, is surrounded by the most important architectural features: the 12th century Cathedral of San Cerbone; the museum with important Siena Renaissance masterpieces (e.g. Ambrogio Lorenzetti) and documents and writings concerning the necropolis and Etruscan settlements discovered in the area (Lake Accesa). LAKE ACCESA is a small lake ten kilometres from Massa Marittima. Its interest lies not only in the singularly beautiful setting but also in the important archaeological findings uncovered in the surrounding area.
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From the main road (S.S. 440) which leads to Porto Santo Stefano a turn off takes visitors to the mountain of Monte Argentario, linked to the mainland by two strips of land, the Tombolo della Feniglia to the south and Giannella to the north. Mount Argentario has been inhabited since the Iron Age, ruled by the Aldobrandeschi family in the 13th century, conquered by Siena and occupied by the French in the 18th century and it affords some spectacular panoramas. The Passionist Monastery was built by San Paolo della Croce in 1720.
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The small town of Montecucco is mentioned as far back as 1106 when it was recorded as a donation to the Abbey of San Salvatore and again in 1274. However, no traces of these ancient settlements remain today. There is currently a farming estate composed of a manor-type house and outbuildings with olive mill set around a courtyard and the Chapel of Sant’Antonio Abate, 1941-43.
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This is part of the local district of Roccastrada and is mentioned for the first time in 1076. It belonged to the Longobard Aldobrandeschi family until 1260 when they were forced to surrender to Siena. In 1328 the castle was conquered by Castruccio Castracani degli Antelminelli who rebelled agianst Siena but was then forced to surrender to Siena’s siege for repossession of the Rocca. The historic centre of Montemassi is delightfully picturesque and retains all the characteristics of a real medieval town nestling below the Castle.
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In the town of Montepescali we recommend a visit to: the Romanesque Church of San Niccolò, dating to the 10th-11th century, situated in the highest part of the town in defence of the walls. Inside the church there are several paintings, frescoes, an elegant wooden 14th century crucifix and a marble Holy Oil tabernacle dated 1614.The most important work is the beautiful 15th century “pala” or altar-plate depicting the Madonna on the Throne with Holy Child and saints, attributed to Matteo di Giovanni and dated approximately 1480.
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