This study follows the multiple migrations of a middle class 'Portuguese'/'Macanese' family in two imperial contexts and explores the complex relationship between 'race', 'class' and social mobility as wider social experiences shaped by imperial traditions, personal ambitions, social networks, and identity transformations. Through an examination of four generations of the Pereira family, from the late seventeenth century to the early twentieth century, I trace their movement from Portugal to Portuguese Macau to British Hong Kong, and finally to Britain, in order to reveal the shifting meanings and strategic value of being 'Portuguese', 'Macanese', and 'British' under different social settings and timeframes. Ultimately, this study aims, through the lens of middle-class migrants, to understand the construct of 'race' beyond the coloniser-colonised spectrum and to reconsider the colonial encounter as a pragmatic response to migration opportunities, social traditions and life challenges.