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The reason for studying this interaction between Europe and Kaliningrad is multilayered. Kaliningrad is even today in a tricky position, its complex past and present cause it great uncertainty. The Kremlin on the political level is carefully controlling this former Prussian–Soviet exclave. However, Europe surrounds the area. In essence, European interaction has caused European ideas, money, and culture to seep back into the Kaliningrad territory. Kaliningrad enjoyed its European connections. On the other hand, it felt alienated by Russia's isolationist and anti-separatist policies over the years. Since 2014, this interaction has been complicated by Russian and European disagreements about the annexation of Crimea. This document examines the connections between Kaliningrad and Europe from the collapse of the Soviet Union to 2016. The development of this fascinating interaction between a Russian exclave and the west is presented in the introduction of this paper. The exact link being under scrutiny are economic ties with Europe. Two sub-themes were examined completed in order to further explain in more detail the relationship between the two entities. For economic ties, the author discusses the internationalization of the formerly local economy of Kaliningrad and tourism. In addition to these two, the conclusion expresses the author's belief on what has occurred and why. For the research of the aforementioned subject, various sources were used. Both western and Russian archives, official documents, official information, academic journals, books, and respected mass media resources were utilized.