A method and mobile transceiver with adaptive monitoring are provided. In accordance with one embodiment, there is provided a method of operating a mobile transceiver, comprising: waking up the mobile transceiver from a low power mode in response to a wakeup event; determining a waypoint in a travel itinerary corresponding to the wakeup event, the travel itinerary defining a number of waypoints including an origin endpoint and destination endpoint; performing an action associated with the wakeup event; determining a wakeup frequency associated with the determined waypoint; and setting a wakeup frequency of one or more subsequent wakeup events in accordance with the determined wakeup frequency.