A unique routing system and method that facilitates adjusting waypoint locations to optimize a cost function and presenting more relevant contextual advertisements based in part on the waypoint locations. The system and method involve examining waypoint locations including a start, end, and any in-between waypoint to determine whether they are reachable or routable according to the preferred mode of transportation. Adjustments can be made to one or more of the waypoint locations in order to accommodate this mode of transportation in view of a given cost function. Adjustments can be made that optimize the cost function to minimize overall costs. Multi-modal routing can be initiated as well to configure a route using the selected or adjusted waypoints and multiple modes of transportation in order to optimize the cost function. Adjustments and the selection of contextual advertisements can be based on user intention and several other route related factors.