It is said that during twentieth century more momentous events occurred in history of mankind than in previous nineteen centuries; not for nothing did Erick Hobsbawn place so much emphasis on analyzing transformative processes of what he would call the short twentieth century[1]. It is undeniable that it was a short, but at same time a turbulent period. But if planet was shaken several times in 20th century and so far in 21st century, island nation of Cuba has felt much more intensely reverberations of world changes in last hundred years, which in turn has affected its relationship with itself, as well as its regional and global context. The following lines provide a brief summary of Cuban geopolitics from period prior to 1959 Revolution until resignation of Fidel Castro as president of Cuba in 2008. The purpose is to show how, in spite of prevailing ideologies at different historical moments and impact they had on Cuba's relationship with its environment and world, island's particular geographic location is most important factor in geopolitics of this country since its independence in 1898. Translated with www.DeepL.com/Translator (free version)