Abstract: A method and system of determining cost of automobile insurance based on safety characteristics of road segments comprising routes expected to be followed on trips insured vehicle and driver have made or are expected to make over the time period the insurance contract is in force. The method comprises steps of identifying the trips, selecting routes expected to be followed on the said trips, determining the probability of each selected route being followed on a trip, evaluating the safety characteristics of roads comprising the routes, consolidating the route safety information with the assigned route probabilities and other risk classifications to produce cost of insurance for the identified trips. The results are further consolidated with the cost of insurance due to risk exposures other than those of the identified trips to produce a final insurance cost.