The world’s urban populations are ageing rapidly and there is a pressing need to examine the needs and experiences of older adults in the city. There is additionally a crucial need to understand the pointedly gendered dynamics of the ageing process in the city. This research begins a critical investigation into this topic in Toronto from a feminist perspective, using a strengths-based perspective to examine the experiences of 9 older women living in the west end of Toronto and navigating the urban environment. It also uses insights from 2 service providers who work with older women in Toronto. The paper then engages these findings with an analysis of two policy documents designed to address ageing in the city, the World Health Organization’s “Global Age-Friendly Cities: A Guide” (2007) and the City of Toronto’s “Toronto Seniors Strategy: Towards an Age-Friendly City” (2011), and discusses some revealing discrepancies. It finds significant strengths and considerations that the research subjects harness and navigate in the urban environment, as well as important intersections between age, gender, race, income and immigration status. It discusses the care responsibilities of many of the women and how they affect their interactions with the urban environment. The paper also points to directions for future research to better understand the ageing process from a critical, intersectional perspective and locate it in a current discussion of urban theory.