A method and system for generating optimal itineraries based on network connectivity. A computer receives a first message from which a current position of a vehicle on a trip, destination, service(s) being provided to mobile device(s) in the vehicle, service provider(s) and network(s) are extracted. Optimal itineraries are generated by generating sets of optimal parameters that include paths for which connectivity measures satisfy predefined criteria and hops that indicate positions associated with connectivity changes. A response to the first message indicates the optimal itineraries and the associated sets of optimal parameters and is sent to a vehicle-based device. Sending the response results in the mobile device(s) making the connectivity changes when the vehicle is detected at the hops.