The following study deals with Aristippusʼ philosophy of hedonism and it is divided into three main parts. In the first part we analyse the problematic relation between Aristippusʼ philosophy and Socratic tradition of thought. In the second part we identify the possible affinity between Aristippusʼ philosophy and the so-called Sicilian way of life and we argue that Aristippusʼ hedonism represents a peculiar blend of Socratic and Sicilian philosophical tenets. In the third part we focus on crucial and fundamental theoretical notions that define metaphysical, ethical and epistemological aspects of Aristippusʼ philosophy. We identify three distinct features of Aristippean hedonism, namely presentism, aprudentialism and ethical hedonism. In the conclusive part of the study, we focus on the notion of situationism as another important feature of Aristippusʼ philosophy and propose to label his philosophy as ‘situationist hedonism’.