This paper presents an empirical study aiming at investigating individual differences and behavioral aspects involved in modeling web navigation. Factors that have an influence on web navigation behavior were identified with the aid of task analysis and their relevance in predicting task outcomes (performance, satisfaction, disorientation) was tested with the aid of multiple regression analysis. Several types of navigation metrics were calculated based on web logging data and used as indicators of user characteristics and task outcomes. Results show that spatial-semantic cognitive mechanisms seem to be crucial in adequately performing web navigation tasks. The fact that user characteristics and task outcomes can be estimated with reasonable accuracy based on navigation metrics suggests the possibility of building adaptive navigation support in web applications.