How to reach
The castle of Montemassi rises in the municipality of Roccastrada, province of Grosseto, on a hill 280 mt. high, at the borders of the northern part of the grossetana lowland. It can be reached from north (Florence) following the motorway Florence-Siena until the exit 'Civitella Marittima' then continuing on the road SS223 toward Grosseto. It is around 23 km. far from of the motorway exit.
The castle is, without any doubt, the most famous monument in the territory of Roccastrada, for its importance of historical document (it was represented on the famous fresco situated in the public palace of Siena attributed to Simone Martini) and for the high example of Gothic style architecture that it represents. The fortification, that crowns a hill above the little hamlet, is constituted by two principal parts. At north there's the keep with numerous windows, loopholes and the rests of a polygonal tower. The external coverage and the inside floors were probably in wood. The building also contains a big water cistern. At south we can find the ruins of a square tower with loopholes along its walls and rests of fine internal stone masonry works.
Montemassi is remembered for the first time in history in the year 1076 as ownership of a certain Count Ildebrando. During the 13th century the castle belonged to the powerful Aldobrandeschi family and, between the numerous fortresses that they ruled in the Maremma, it was one of their main stronghold. In 1306 the castle wad subdued to the Pannocchieschi family that had numerous territories in the northwestern part of Tuscany. In the year 1328, with the support of Castruccio Castracani of the Antelminelli, the castle revolt against Siena but the powerful Sienese army reconquered, after a long siege, the fortress (this is the event celebrated by the fresco of Simone Martini above named). The Republic gave the castle in fief to the Salimbeni family (see also Rocca of Tentennano); they lost it in 1375 after a failed rebellion against the central power.
Subsequently the castle was sold, and maintained then for seven years, to Mino Verdelli for 800 Florins; then passed again to the Republic of Siena, in 1404 was decided to dismantle the fortification, to avoid that some rebels made it a base to oppose the Sienese dominion.
Ferdinando II of Tuscany, with a document of September 19th 1632, assigned Montemassi in fief to Giovanni Cristofani Malaspina da Mulazzo. On April 7th 1770 The Malaspina sold the castle to the Marquis Domenico Cambiaso da Genova and it was left to ruin. Today the whole complex lies in a state of heavily degrade.
The historical center of Montemassi is very picturesque and still maintains today the aspect of a compact medieval hamlet at 'pine-cone' form; there are no more traces of the city walls, at exception of a gate, that once were connected with the castle.
During July 2007 was completed the external restoration of the Palace/Keep and secured the staircase that leads on the panoramic platform above the water cistern. In June 2008 has been aquired by the Municipality also the South Tower (or A Tower), and 250.000 Eur were assigned for its restoration and new archeological excavations. The restoration has begun in November 2008 and ended in January 2010.
Aerial photos used under permission by Opaxir: https://www.flickr.com/photos/opaxir/
More info & notes
Montemassi from the air: