The Port Bastion was the last one of the pentagonal fortification that was built; his construction, done in 1574, definitely concretise the will, expressed by Guidobaldo II from the Rovere, to extend the city beyond the river. The Duke wanted to make Senigallia his ideal city and chose to leave to posterity memory of him through the built of a great work: a fortified wall.
The choice of the pentagonal configuration of the enclosure, declared as a perfect form to defense, was close at the renaissance culture for the related five summits of the human figure: the head, two hands and two feet. This form will be taken as a model to create fortified citadels that will proliferate in all the italian and European cities between the seventeenth and the eighteenth century.
For the first time in his urban history, Senigallia chose to enclose the Misa within the walled perimeter, making a new neighborhood. The organization of the city, in this side, had to contain a series of blocks with living buildings functional warehouses in the period of the Fair of the Maddalena at the end of July.