The role of smart cities in order to improve older people’s quality of life, sustainability and opportunities, accessibility, mobility, and connectivity is increasing and acknowledged in public policy and private sector strategies in countries all over the world. Smart cities are one of the technological-driven initiatives that may help create an age-friendly city. Few research studies have analysed emerging countries in terms of their national strategies on smart or age-friendly cities. In this study, Romania which is predicted to become one of the most ageing countries in the European Union is used as a case study. Through document analysis, current initiatives at the local, regional, and national level addressing the issue of smart and age-friendly cities in Romania are investigated. In addition, a case study is presented to indicate possible ways of the smart cities initiatives to target and involve older adults. The role of different stakeholders is analysed in terms of whether initiatives are fragmentary or sustainable over time, and the importance of some key factors, such as private–public partnerships and transnational bodies. The results are discussed revealing the particularities of the smart cities initiatives in Romania in the time frame 2012–2020, which to date, have limited connection to the age-friendly cities agenda. Based on the findings, a set of recommendations are formulated to move the agenda forward.