This is the oldest and best conserved of the City’s gates. Although it is not certain, some of its elements, such as the perfect isodomic construction, make us think that the gate was built in pre- Roman times. The blocks placed at the head and the sides follow an alternating pattern typical of buildings of Hellenic character to be found in other areas of the city.
It is also still possible to see that the gate had a double locking system following the curve of ascent. There is a legend about this gate, lost in Sorrento mythology. The 13th June 1558 was one of the darkest moments of modern history for the city of Sorrento. A fleet of around 100 Saracen ships, after having ransacked the hamlets of Massa Lubrense, sailed into the Bay of Sorrento. That night the “furies of the sea” managed to enter and plunder Sorrento, despite the massive walls, because the gate was opened by an Ottoman slave, in the service of the Correale family. According to the chronicles, the Correale family had custody of the 4 keys to the 4 gates and it seems that the slave stole the key to the northern gate, allowing the marauders to enter. The day of Sant’Antonio in1558 is still remembered by the local inhabitants of Massa Lubrense and Sorrento as one of the saddest in their history.