The purpose of this paper is to show the results of the analysis of placenames used in Macedonian texts translated to Italian from the point of view of their relationship to the Macedonian cultural reality. The analysis is focused on two major problems: translatability of toponyms and the possible translation strategies. The choice of the translators is illustrated with examples taken from the texts of Macedonian narrative translated in to Italian. Three different types of translation strategies are identified: transliteration, semantic recreation and explicitation. In some specific and difficult cases the name of one place can be found in different variations in texts of different translators and the cultural allusions that arise as a consequence.