This essay examines how the Manila-Acapulco galleon era (1565-1815) under Spanish colonialism forged the early mestizaje between Filipino Indio men and Mexican Indian and mixed race women, which produced children who became the first multiethnic Mexican-Filipinos in Nueva España (Mexico). This story is juxtaposed with current migrations of Filipinos to Mexico via the vacation cruise liners, which share a story of contemporary mixing between Filipinos and Mexicans. By acknowledging both their identities and looking to the past, these modern day multiethnic Mexipinos and Filipinos connect to a long historical web of interconnectedness which underpins the mestizaje that began in the sixteenth century.