For the people of Vilnius, it is helpful to consider its image in the eyes of strangers. They reflect the strangeness of Vilnius itself. The concept of strangeness will be developed by considering the related spectrum of these strangers' acquaintance with the city. We consider images of Vilnius formed by noteworthy Europeans who passed through there or spent some part of their life there, such as Napoleon Bonaparte, Romain Gary, Fyodor Dostoyevsky, Lev Tolstoy, Josif Brodsky, Mikhail Bakhtin, Vladimir Toporov, Aron Gurwitsch, and Czesław Miłosz. For some of them (Napoleon, F. Dostoyevsky), Vilnius was strange as a not yet assimilated territory. For others (L. Tolstoy, J. Brodsky), Vilnius was an important point of transition between geopolitical spheres. For some of them (R. Gary, M. Bakhtin), Vilnius was the environment of their maturation and a springboard to other cities. Vilnius has also been a city of studies and science (for J. G. A. Forster, Cz. Miłosz), a city that formed philosophical attitudes (M. Bakhtin, A. Gurwitsch), and a city of heritages: Russian (for F. Dostoyevsky, L. Tolstoy), Polish (Cz. Miłosz), German (A. Döblin, J. G. A. Forster), Jewish (A. Gurwitsch), pagan (V. Toporov). By appealing to the above mentioned images, the paper deals with philosophical aspects of strangeness, regionalism, and urban environments.