In a life course perspective, the transition towards retirement can be seen as a process that unfolds over a particular period of time rather than being an instantaneous exit from active professional life. Previous research demonstrates that retirement timing and trajectories result from a complex interplay between individual and institutional factors. Within the debate on the progressive de-standardization of the life course, early-retirement behavior has to be studied as the outcome a voluntary choice driven by preferences given the range pension schemes available. In Italy several reforms have been implemented since the early 1990s to moderate the massive (compared to other European countries) use of early-retirement. Despite the widespread of the “early-exit” culture, no research exists for Italy on the role of individual preferences on retirement decisions. In this paper, we focus on Italy by using SHARE data to describe the relationship between early-retirement preferences and actual behaviors. We explore this association for men and women and according to educational level. Moreover, we use sequence discrepancy analysis to study the strength of the relationship between longitudinal retirement trajectories and preference for early-retirement. Our results show that the probability of early-retirement is positively associated i) with being a man instead of a woman and ii) low and medium education, as well as iii) with positive preferences for early-exit. Finally, while we did not find differences among men, we found more variability in retirement trajectories of those women who expressed negative preference for early-retirement, probably due to the prevalence of self-employees among them.