Abstract: The transportation system and method includes a server in communication with a user and a vehicle via a wired or wireless data channel. The user provides the server with transportation request information, and requests transportation options from the server. The user may seek transportation either for a passenger or for a package or other item to be transported for delivery to a specified destination. The server evaluates the transportation request information provided by the user and determines transportation options, including available routes of travel (times, paths, etc.) and the charges associated with the various available routes of travel. The server notifies the user of transportation options, including available routes of travel and associated charges. The user selects one of the transportation options and requests transportation according to the specified travel parameters. The server books the requested transportation and notifies the transporting vehicle of the new transportation assignment.