The article focuses on allegory as a figurative expression of an abstract notion, designed to instruct, preach, or teach. It provides insights into its semantics, different from metaphor and symbol, and discusses how it was evolved by ancient and medieval philosophers. Allegorisation can be regarded through a single word or a chain of judgments. An example in question is the poetry and prose of the Portuguese playwright and poet Jil Vicente. To illustrate this, the article analyzes the JOURNEY concept in Vicente’s works.