While regional cooperation has grown throughout most parts of the world since the end of the Cold War, the Kuril Islands conflict between Russia and Japan has so far been blocking off prospects for the establishment of stronger crosscultural ties between the two countries. The status quo of low-profile diplomacy on the national level seems to lie in the interests of both sides for the time being, but the Japanese port cities near the Okhotsk Sea could benefit on various levels from enhanced cooperation with the island that is geographically closer to them than Tokyo, the Russian island of Sakhalin. At the same time, they are the main linkage locations of cross-cultural communication between Russian visitors and Japanese communities. For this reason, an analysis of the main elements of the bilateral exchange on a local level may add to an understanding of the functioning of ‘transculturation’ processes, and at the same time make it possible to assess the possibilities of the development of some kind of a regional consciousness as the basis for stable and sustainable collective security in the area of the Okhotsk Sea.