Present paper is aimed at assessing the state of Japan’s cultural diplomacy to the Russian Federation after 2014 as this period is signified by “the turn to the East” in Russian foreign policy and the emergence of positive context for Japanese soft power in Russian society. A number of important events in cultural ties between Japan and Russia in the past five years are highlighted. Critical assessment of these developments and their outcomes shows that there are certain challenges as well as opportunities for the intensification of Japanese cultural diplomacy to Russia.