Electric, plug-in electric and plug-in hybrid electric vehicles (xEVs) are receiving a global attention from automotive industries, vehicle vendors, R&D organizations, power sectors and policymakers in the intelligent transportation era. Penetration of xEV fleet into the contemporary charging infrastructure(s) in the absence of robust integration network imbalances the power grid and potentially jeopardize the execution of emerging distributed generation systems. However, smart grid technologies in collaboration with smart charging management strategies can circumvent such operational disparities, thus enabling a reliable, efficient, consistent and optimal electric energy management in the power system. This work employs the notion of Cloud of Things (CoT) to propose a comprehensive cloud aware Transport Oriented Smart City (TOSC) framework intended to provide intelligent solutions to the contemporary transportation infrastructures in the emerging sustainable smart cities. The proposed work also demonstrates a commercially viable vehicle to cloud (V2C) fleet charging framework for charging management of xEVs through micro grids/ smart grid. The unprecedented data breeding across V2C, cloud to grid (C2G) and grid to vehicle (G2V) bidirectional communication interfaces elucidates the need for computationally efficient analytics. A state-of-the-art Big-Data to Knowledge (B2K) workflow structure is thus proposed for translating the generated data into efficient knowledge for noble decisions and inferences. Finally, the substantial Mobility as a service (MaaS) adoption challenges and data science prospects are outlined along with the emerging technologies that can co-work with the proposed framework to ensure commercial viability and optimal implementation in emerging TOSCs.