The first fortification of Massa Marittima was the so-called Castle of Monteregio (situated on the place where is today the Hospital of S. Andrea in the New City), it was the residence of the Bishops of Massa beginning from the 9th-10th century, subsequently, the bishop Alberto, at the end of 12th century, extended the fortifications around the Castle, with a large town walls with towers and gates, the last survivor gate of these first works of fortification was the Gate of San Pietro, that was demolished in 1851, it has inscribed the date 1206.  

In the course of 13th century the town-walls seems to have been enlarged until embrace the Convent of San Francesco and the Church of San Rocco, later in 14th century, instead the extension of walls was reduced until the actual dimensions. With the born (31 July 1225) of the Free Municipality of Massa Marittima, it was constructed, in 1228, nerby the castle of the Bishops the powerful Torre del Candeliere (or of the Clock). The Tower nearly was demolished from Siena, but then they keep it, but only two thirds of the original height.

After the occupation of the Republic of Siena (1335), Siena began to built the Senese Fortress, a huge work of fortification that acted as pivot between the two parts of the city (Old City and New City), it divided the two parts of the city with two imposing curtains of walls, nearly parallels, fortified with towers, rivellini and bastions. The Torre del Candeliere, in 1337, was joined to this new work of fortification by an imposing arc-bridge that measure 21,79 meters of rope. Next it's the double door that connected the Old City with the New City, the Porta alle Silici, the most beautiful door of Massa Marittima, it go back up to 14th century and an insciption over the arc indicate that the works of fortification of the Fortezza Senese were finished on 19 February 1337. Beyond the Porta alle Silici we entered in the New City built in 13th-14th centuries. After the rebellion of the massetani, in 1355, the senesi demolished a tract of walls that included the Convent of San Francesco and in 1377 the extension of walls in the New City was newly reduced with the construction of the double Gate of San Francesco (1377) and of the Gate of San Rocco, that replaced the previous Gate of Bufalona, that was situated near the Church of San Rocco.  

The Torre del Candeliere it is the only remain of the old fortress constructed from the Free Massa Municipality in 1228. The Torre del Candeliere and the Senese Fortress are visitable, from both are enjoyed a fabulous panorama on the city, the surrounding campaign and the coast. Between the gates still remained in the Old City are: the Porta del Salnitro (in origin also this a double gate, the inner one was demolished in 1781), the Porta San Bernardino , the Porta San Rocco and the Porta dell'Abbondanza. In the New City are: the Porta alle Silici, the Porta San Francesco and the Porta Eleonora. Nearby the Porta San Francesco is one of the tract better conserved of the town-walls.  

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Detail of the Porta alle Silici, Massa Marittima, Grosseto
The Sienese Fortress, the Torre del Candeliere (Tower of Candlestick) and the arch-bridge that connects them, Massa Marittima, Grosseto
Part of the walls of the Sienese Fortress, Massa Marittima, Grosseto	Interior of the Torre del Candeliere (Tower of Candlestick), Massa Marittima, Grosseto	Porta San Rocco (outer side), Massa Marittima, Grosseto
Porta al Salnitro (outer side), Massa Marittima, Grosseto	The arch-bridge and its junction to the Sienese Fortress, Massa Marittima, Grosseto	Porta al Salnitro (inside), Massa Marittima, Grosseto