The demographic grand challenge of population ageing will be reflected in most areas of society and, to a great extent, in the area of transportation as well. It will have an impact on, for example, travel demand, infrastructure needs, traffic safety and the climate. The post-World War II cohorts, the so-called “baby boomers”, will comprise a large share of tomorrow’s older population, and it is expected that they will differ from their parents’ generation when they grow old. In order to better understand how the ageing baby boomers may affect future travel demand, the travel behaviour and expectations of Danish baby boomers were analysed based on 1772 standardised telephone interviews. In general, the baby boomers reported being healthy, independent and highly (auto)mobile. They were also optimistic regarding their level of mobility, capability to use a variety of travel modes and ability to lead an independent life in the future. However, there were significant gender differences in terms of present and expected car use in old age, which were somewhat similar to those observed in older cohorts. In addition, different sub groups of baby boomers could be identified based on their future expectations: the so-called Flexibles, Independents and Restricted subjects. The segments showed significant differences in current travel behaviour and living conditions, as well as some similarities to former segments of older road users. The results indicate that the baby boomers are likely to be strong consumers of the transport system also as they age, but that the group is also heterogeneous. Thus, overly optimistic scenarios about independent baby boomers who differ from the previous generations and whose need for external support in old age will be minimal may be unrealistic.