In the early Middle Ages on the territory of the Khazar Khaganate the waterway from the Black Sea to the Caspian Sea existed thanks to a land portage for ships in the place of closest convergence of the Volga and the Don rivers (60–80 km). However, there is still no consensus on some issues related to the functioning of this communication. Therefore, the purpose of this article is to provide answers to them. In the main part of this research, a comparative analysis was carried out: the data of Muslim geographers of the 9th – 10th centuries AD were compared with the information from Christian authors on the navigation in Europe and West Asia. The Ancient maps and archaeological data were used as well. As a result, we can establish the following: already during the 40th years of the 9th century AD the Volga-Don land portage for ships began to function again, that coincided with the first voyages of the Rus’; in spite of common opinion, the route of ship dragging could pass from a springhead of an affluent of the Don river to the main stream of the Volga river (20 km); in the 9th century AD the Rus’ people could transport their ships with the help of special devices, and by a simple drag in the 10th century AD; therefore, in the 9th century AD their ships could be commercial, and in the 10th century AD they could be only military and light; at the place of transfer the protection of ships from attacks by nomads was ensured by the Khazars fortresses and also military garrisons at fords across the Don river. Thus, in the 9th century AD the Rus’ain people and the Khazars used the ship portages as trading partners and then in the 10th century AD the Rus’ people already thanks to the ship portages began to attack the Khazars.
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