This thesis consists of five annotated translations, accompanied by a discussion. The translations are excerpts from three books, one guidebook and several summaries of systematic reviews in the sphere of healthcare. Excerpts from books Cultures and Organizations: Software of the Mind. Intercultural Cooperation and Its Importance for Survival by G. Hofstede, G.J. Hofstede and Minkov, M., and A University Education by D. Willets were translated from English into Croatian, as well as Plain Language Summaries of Cochrane Reviews. Excerpts from the guidebook for the permanent exhibition of the Greek and Roman collection of the Archaeological Museum in Zagreb, as well as short story Rupa puna dima by Andrija Škare, published in the book Društvene Igre, were translated from Croatian into English. The discussion explores culture-specific items (CSIs) in literary translation on the example of the translation of A. Škare’s short story Rupa puna dima. The theoretical framework of the discussion emphasizes various criteria that have to be taken into account during translation, such as text-orientation and translation norms. Given that each translation of a CSI is a particular translational situation, the analysis shows a wide range and complexity of the decision-making process during translation.