A method includes transmitting, to a driver computing device associated with a driver, navigational data to direct the driver to a first pick-up location and to direct the driver from the first pick-up location to a first drop-off location along a first route to fulfill a first transportation request associated with a first user. The method further includes determining that the first route is to be modified, identifying a drop-off area associated with the first drop-off location, and selecting a second drop-off location and a second route for the first user. The first drop-off location and the second drop-off location are located within the drop-off area. The method further includes transmitting, to the driver computing device, updated navigational data to direct the driver to the second drop-off location along the second route to fulfill the first transportation request.