This study presents a diachronic analysis of the terms encoding the four cardinal directions in 54 Philippine languages. The direction terms vary greatly in the languages, making it impossible to reconstruct a single directional system for the Philippines. However, it was found that four major fields of reference are used in encoding directions—the path of the sun, the distinction between land and sea, the wind/monsoon systems, and systems of location. While these orienting features can be found across languages from different families, the idiosyncratic use of the land-sea axis and the monsoon systems in the Philippine (and Austronesian) languages are indicative of the lives and practices of the speakers as seafarers. Moreover, based on a typological classification of the terms, we can observe certain implicational relationships in the lexical encoding of directions, that is, the east-west axis tends to be encoded first before the north-south axis, given the contiguity of the former axis to the movement of the sun, a feature that is naturally salient in all speech communities.