Innovations such as the Cloud, Internet of Things (IoT), and data analytics have already dramatically altered the customer experience in many, if not all, industries. Blockchain, as another emerging technology, is expected to be the next generation infrastructure to established trusted multiparty collaborations. In this paper, we investigated the convergence of aforementioned technologies, by presenting a prototype of fine-grained transportation insurance. Insurance premium were assessed based on vehicle's usage and driver's behavior, which were deduced from streaming IoT data collected from mobile sensors. This incentive mechanism promotes fairness among drivers and encourages safer driving style. The prototype takes advantage of both private blockchain (e.g., high transaction rate in Hyperledger) and public blockchain (e.g., inbuilt cryptocurrency). Besides system architecture and implementation details, preliminary performance evaluations are presented and discussed.