Methods and systems for offering and providing trip-based vehicle insurance are provided. Information is received regarding a vehicle operator and a vehicle, and trip-based insurance policies including quantities of vehicle use units are offered to the customer. Based on selected coverage types, the insurance provider may generate an insurance quote for a policy having an amount of the vehicle use units and may facilitate a purchase transaction with the customer for the insurance policy. Once a policy is selected and purchased, the system and method monitor vehicle use to determine each use of a vehicle use unit. Each vehicle use unit generally corresponds to one vehicle trip, but additional vehicle trip limitations may be added that may result in additional charges when exceeded during the course of a vehicle trip.