As a result of the Ukrainian authorities' refusal to sign an agreement on joining the EU, at the end of 2013 protests were held in Kiev and a number of cities, led by pro-West opposition. The political situation was radicalized, resulting in the overthrow of the regime of President Yanukovych. These developments triggered protests in the Crimea and in the southeastern regions. After the referendum, Crimea unilaterally separated from Ukraine and joined Russia, while an armed conflict between the central authorities and the armed groups of rebelled pro-Russia population began in parts of Donetsk and Luhansk regions. Ukraine accused Russia of annexing the Crimea and of Russia's armed formations actively fighting on the side of the pro-Russia separatists. Bilateral relations were minimized, and have continued in that way for the last two years, with the emergence of a large number of problems that have further burdened and accentuated existing differences of views. Additionally, the newly-established status of Crimea has considerably worsened Russia's relations with Western countries and radicalized the security situation at the regional and global levels. The complexity and topicality of the 'Crimean question' is defined, inter alia, by the special geostrategic significance of the Crimean peninsula, as well as the specific geographical, historical and cultural-identity characteristics of the area. With great care not to fall into the trap of geographical and historical determinism, the paper seeks to prove that the physical and geographical and socio-geographical characteristics of Crimea, as well as its specific historical development, are elements that influenced the change of its status (unilateral separation from Ukraine and joining Russia), causing the creation of a complex political and security situation in the Black Sea region, which threatens to disintegrate the entire system of regional stability, with possible implications for global security. The aim of the paper is to point out the importance of the 'Crimean question' that significantly determines the security of the region and the relations of the most influential geopolitical actors, through the insight in the geostrategic position of Crimea. The aim is also to draw attention to the current topic and to communicate it to the general public, namely, to make, in an affirmative way, a theoretical shift towards understanding and critical perception of the 'Crimean issue', mainly from the perspective of the events of the last two years.