This study explores whether the plans of older workers on the cusp of retirement are in line with the active ageing agenda set by policy makers in Europe. The study was carried out in Italy, England, and the United States of America (USA). A total of 133 older workers who planned to retire within the next 10–12 months were interviewed (55 in England, 40 in Italy and 38 in the USA) between May 2014 and early 2015 using common semi-structured questions. Active Ageing Index dimensions were used to gauge the orientation of older people towards their retirement. The results of the study suggest that, with some differences, retirement plans of interviewees were substantially consistent with the active ageing perspective. However, some challenges were highlighted, including the need for governments to do more to promote genuine freedom of choice in relation to leaving the labour market, and to provide greater support for informal family carers. Findings also pointed to the need to measure active ageing in connection with individual wellbeing, e.g. by including indicators of leisure activities and by considering the re-weighting of employment and informal care dimensions. Companies could also provide more support during the retirement transition, with opportunities for maintained social connection with former colleagues, and help in making and fulfilling retirement plans.