This article aimed to explore the perspectives and experiences of women and men at the stage in their lives following professional retirement, enriching the present and future of a continuously ageing Portuguese society. In order to better capture the diversity and complexity of each individual’s experiences, a qualitative methodology was used. Semi-structured individual interviews were carried out with sixteen retired people, eight women and eight men, aged between 59 and 88 years old. A thematic analysis allowed us to identify five themes in the interviewees’ discourses. We concluded that gender may be a source of heterogeneity at this stage of life, suggesting that these findings should be analysed in the scope of a life course perspective, and highlighting the impact that the different trajectories of women and men have, as well as the historical and social context in which they take place.