Derbent
While Derbent is certainly Russia’s most southern city, it also makes a good case for being its oldest - although since the inclusion of Crimea this title is not so clear with rival claims from Kerch. Derbent is nevertheless undoubtedly a very ancient place dating back to the Classical Era. It’s located on what is known as the Gates of the Caspian - a narrow strip of land between the Caucasus Mountains and the Caspian Sea - has meant that is has always been of ultimate strategic significance in controlling the passing of troops between the Eurasian steppe and the Iranian Plateau. Some experts even associate Derbent with the Gates of Alexander of Greek Legend, which would date the city to the time of Alexander the Great to the 4th century BCE.
The name Debent translates from the Persian as Barred Gates and it is during the reign of the Persians that the modern city really began to develop. The Naryn-Kala fortress which has survived to this day, dates from the 8th century onwards. This site and the additional fortified walls are the highlight of visiting this fascinating city on the Caspian.