Driver heterogeneity in travel behavior has repeatedly been cited in the literature as a limitation that needs to be addressed. In this work, driver heterogeneity is addressed from four different perspectives. First, driver heterogeneity is addressed by models of driver perceptions of travel conditions: travel distance, time, and speed. Second, it is addressed from the perspective of driver learning trends and models of driver-types. Driver type is not commonly used in the vernacular of transportation engineering. It is a term that was developed in this work to reflect driver aggressiveness in route switching behavior. It may be interpreted as analogous to the commonly known personality-types, but applied to driver behavior. Third, driver heterogeneity is addressed via latent class choice models. Last, personality traits were found significant in all estimated models. The first three adopted perspectives were modeled as functions of variables of driver demographics, personality traits, and choice situation characteristics. The work is based on three datasets: a driving simulator experiment, an in situ driving experiment in real-world conditions, and a naturalistic real-life driving experiment. In total, the results are based on three experiments, 109 drivers, 74 route choice situations, and 8,644 route choices. It is assuring that results from all three experiments were found to be highly consistent. Discrepancies between predictions of network-oriented traffic assignment models and observed route choice percentages were identified and incorporating variables of driver heterogeneity were found to improve route choice model performance. Variables from all three groups: driver demographics, personality traits, and choice situation characteristics, were found significant in all considered models for driver heterogeneity. However, it is extremely interesting that all five variables of driver personality traits were found to be, in general, as significant as, and frequently more significant than, variables of trip characteristics – such as travel time. Neuroticism, extraversion and conscientiousness were found to increase route switching behavior, and openness to experience and agreeable were found to decrease route switching behavior. In addition, as expected, travel time was found to be highly significant in the models that were developed. However, unexpectedly, travel speed was also found to be highly significant, and travel distance was not as significant as expected. Results of this work are highly promising for the future of understanding and modeling of heterogeneity of human travel behavior, as well as for identifying target markets and the future of intelligent transportation systems.