Women and men often do not experience equal mobility opportunities in their societies. Increasingly, gender is being recognized to play a significant role in transport planning, particularly for addressing individual mobility needs in urban and rural areas. By understanding the link between male and female travelers’ preferences, perceived values, and travel behavior, as well as experienced barriers, transport systems could be better tailored to women’s activities and mobility needs by putting the women’s perspective on center stage. Therefore, the objective of this paper is twofold: (1) to perform an in-depth analysis of women’s and men’s travel behavior to scrutinize the difference in perception of the value of travel time derived from travel experience using various transport modes and (2) to identify the significant factors influencing men and women’s travel behavior in terms of transport mode choice. The empirical analysis is based on a multinomial regression model of 1406 female travelers and 1486 male travelers in eight European countries. In regard to the subjective values associated with users’ perception of travel time worthwhileness, this research implies that the perception of enjoyable travel time and the perceived mood from the travel experience would increase the tendency of ridesharing and using private motorized modes of transport as a passenger among women. Results also demonstrate that women have a higher perception of the worthwhileness of travel time for walking compared to men using bicycle and micro-mobility systems and private motorized vehicles as a driver. Regarding public transport, a significant difference in the perceived worthwhileness of travel time between female and male users of public transport in the European urban areas was also discovered.