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Toledo was walled by Romans, and a lot of its stones were reused later in built walls, as the original perimeter was subsequently tripled. The Visigothic King Wamba renewed the Roman fortifications, sculpting in its gates an inscriptions. The inscriptions were destroyed by the Muslims, and restored in 1575 by the Corregidor Juan Gutiérrez Tello.
The Arabs widened the city and the walls. After the Reconquista, the walls were again advanced in outer line and new gates were constructed. The gates and towers of the Walls of Toledo have survived until these days.
References:Herceg Novi was founded (on a former small fishing village, existing since Roman Empire times) as a fortress in 1382 by first Bosnian King Stjepan Tvrtko I and was called Sveti Stefan or Castelnuovo. The Turks conquered Herceg Novi in 1482, and ruled for 200 years, until 1687. However, there was a short pause between 1538 and 1539 when it was held by the Spaniards before they were defeated in the Siege of Castelnuovo. Turkey ruled again until 1687, from then until 1797, the town was ruled by the Venetian Republic.
The Herceg Novi old town is amazing. It is on a fairly steep hill that leads all the way down to the sea. Wandering through the small stairways to the various plazas and fortresses is a many hour adventure.