Methods and systems for determining a safest transportation route include determining a risk value for each of a set of candidate routes between an origin and a destination based on one or more safety factors or criteria, and comparing the risk values to determine the safest route. The risk values may be based upon default or selected safety factors, and may correspond to a normalized cost per unit distance. Safety factors may be derived from map data, obtained from user input and/or derived from other statistical data. User preferences and priorities may be included in the process for determining a safest route. Determined safest routes may be displayed, and may indicate especially risky portions of the determined safest route.