This article examines passages in Sirach which posit that travel fosters understanding and that the sage knows how to travel in foreign lands (Sir. 39:4). The references are discussed in the context of two ancient Mediterranean corpora, i.e., biblical and Greek literature. Although the evidence in Sirach is insufficient for demonstrating the existence of a specific social practice, the text at least attests to an attitude of mental openness, imagining travel as a professional enterprise with positive outcomes. This article argues that the closest parallels to Sir. 34:9-13 and Sir. 39:4 are not to be found in the Hebrew Bible or Hellenistic Jewish literature but in (non-Jewish) Greek writings which refer to travels undertaken by the sages who roam around for the sake of learning. The shared travel motif helps to demonstrate that Sirach belongs to a wider Hellenistic Mediterranean context than just that of biblical literature.