Transnationals constitute one-third of the population of the economically prosperous Singapore. Applying a family language policy (FLP) framework and collaborative autoethnography from data (interviews, videos, and diaries) spanning 13 years, this study delves into the linguistic journey of an Italian-Chinese family with two children born in Singapore. The analysis demonstrates the dynamics of language ideologies, management, and practices, following changes in parental beliefs, children's linguistic proficiencies and agency, availability of resources within the family and the host country, and unexpected events like COVID-19. The article highlights how multilingual parents' ideologies shape up owning to individual experiences, beliefs, and aspirations, and how these ideologies are translated into language choices and day-to-day language maintenance, vis-à-vis Singapore's English-centric policies. This unique longitudinal case study also touches on features pertaining to transnational families in Singapore, such as the perception of the local variety 'Singlish,' caregiving, and schooling options, illustrating the intricate interplay of micro and macro factors governing family multilingualism.