The Penna bastion, also known as San Sebastiano one, was the first to be built during the construction of the pentagonal fortification made by the duke Guidobaldo II della Rovere in 1546.
The fortification, that was already thought by Francesco Maria I, father of Guidobaldo II, is the result of careful studies carried out by the most famous military architects of the era. The political-religious strategy saw the need to equip the cities, especially the ones near the seaside, with a new defensive apparatus, ready to against the Turkish invasions that constantly threatened the Adriatic coast;in this light it was therefore logical that the Duke should begin his fortification on the side from which the greatest dangers came, that was from the sea.
Due to the earthquake of 1930 were implemented some interventions that gradually erased the character of the walled village.
The town plan of 1931 sanctioned the demolition of some buildings, adjacent and internal to the walls, on whose area will be built, in 1936, the elementary school Costanzo Ciano, that today is Giovanni Pascoli, and the Casa del Balilla, then transformed into Gioventù Italiana del Littorio (GIL) and now it’s the seat of municipal offices.
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