Systems and methods relating to usage of multimodal transportation systems are disclosed. Such systems and methods may identify available local transportation modes for a user, such as vehicle-sharing, ridesharing, rental vehicles, taxicabs, owned vehicles, or public transit options. The available transportation modes may be compared, and recommendations may be presented to the user. Routes may be identified, compared, or recommended to a user, and scheduling or ticket purchasing may be facilitated. With user permission, user transportation data may be collected via a smartphone to identify user transportation patterns and preferences, thereby improving recommendations regarding and assessment of user transportation. Information regarding risks or other relevant factors associated with various transportation modes may be assessed for a user based upon typical characteristics of user transportation choices over a plurality of transportation scenarios, which may be indicated by a user transportation profile.