This paper examines how ageing transmigrants engage in practises that serve to decolonise life course in order to create increased opportunities to live well. It analyses the experiences of Jamaican Canadian older adults (age 60 and older) who decided to remain in Canada, return to Jamaica, or travel between countries after retirement. As transmigrants with racialised minority and diasporic backgrounds, they grapple with questions of financial, socio-cultural, and emotional well-being that become more complicated and multi-layered in later life. This qualitative study utilises multi-sited ethnography to collect data in Canada and Jamaica. It also engages with the work of cultural critic Sylvia Wynter whose conceptions of decolonisation and humanism serve to reveal more diversified life course and ageing experiences. As postcolonial nation-states, Canada and Jamaica become ambivalent and vexed sites of home, belonging, security, and movement. Through decolonisation, transmigrants learn and unlearn how to navigate these spaces in ways that illuminate the ongoing struggles and pleasures of the quotidian within the broader contexts of transnational social fields.