An implicit assumption underlying government strategies to achieve a more sustainable urban transportation system is that all automobile users will be encouraged or persuaded to use more “green” transportation: public transportation, walking and cycling. Little consideration has been given as to how sustainable transportation policies and programmess might impact on different age groups in society, including those retired or semi-retired, despite the fact that an unprecedented number of older drivers will be on the highways in the next few decades. There is limited literature on the contextual factors behind their continued reliance on automobiles, their actual driving behavior (e.g., route choice and time of day to drive) framed within the context of social sustainability. This paper introduces the elements of transportation and social sustainability then conducts a comprehensive international literature review focusing on older drivers, their travel choices and associated social sustainability issues. It describes a case study, low-density city and presents empirical evidence, from two surveys conducted in Canberra, Australia. The paper concludes with future research directions that address these issues associated with sustainable transportation.