An individual has their own behavioral patterns that exhibit commonalities over different contexts and situations. Several studies have shown (1) dichotomic human mobility patterns in everyday life such as returner vs. explorer, (2) the analogy of the “Explorer” and the “Web Explorer,” and (3) the same brain structure used during both physical and online navigation. Meanwhile, modern technologies such as smart phones and wearable devices have allowed researchers to collect users’ personal, contextual, and cognitive information and to create behavioral models from different perspectives. Based on the analogy between the physical and online searching, this dissertation investigates individuals’ behaviors during online and physical search tasks to identify their behavioral patterns. To observe the behaviors, during web search task and physical search games, 31 participants’ data was collected via eye-tracker, web browser, and wearable video recorder. Analysis of the behavioral data suggests individuals have preferred searching strategy that they adopt in different tasks and environments. The behavioral pattern, however, was found to be affected by the task type and the way information is structured in the environments.