In this paper, we explore lifetime private mobility milestones in Greece and identify the factors that affect them, to explore the everchanging mobility landscape. In total, five archetypal private mobility milestones were examined: the age of getting a car driving license and the period until getting a car following that; the age of getting a motorbike driving license; the age of getting a first bicycle as an adult; and the age of first traveling by airplane. To this end, duration modeling and namely Kaplan-Meier and Cox Proportional Hazards models were developed. Results show that mobility paradigms are evolving and are affected by a wide array of factors. Generational differences are particularly highlighted, as younger travelers are less likely to get a car driving license or a car sooner but are more likely to get a bicycle as adults. Higher parents’ income diversely affects multiple mobility milestones. Growing up in rural locations and sustainable transport awareness also significantly affect mode choice related mobility milestones. Men were more likely to get both car and motorbike driving licenses at younger ages. The above results highlight the mobility profiles of Greek citizens and the factors that affect them, while offering insights into a future mobility landscape.