Embodiments of the present invention describe systems and methods for automatically generating route(s) based on users' trip intent and conditions. A user enters his/her trip intent and conditions. A context-sensitive route generation system generates one or more routes based on information surrounding the user's trip intent, such as destination, time, means of transportation, purpose and identity(ies) of traveler(s), and conditions, such as user's limitations, needs, and preferences, for the user. Once the user chooses a route to follow, context-sensitive route generation system (CRGS) keeps track of user's movement and can modify the user's route when a need arises. The CRGS searches one or more networks and the system database(s) for profile and real-time (or instant) information for route generation, and continues to mine networks for information related to the trip to ensure the best route is recommended to the user. In one embodiment, profile and real-time information relevant to the trip is used in generating and modifying the route. In addition to generation, monitoring and updating route(s) for the user, the CRGS also can present advertisements of interest to the user for business and services along user's route.