Enterprises are rapidly working on strategies to migrate their applications to cloud. Multi-cloud allows mixing and matching multiple cloud vendors when migrating thousands of applications based on their set of requirements and various different types of constraints. To utilize the advantages of different clouds, achieve maximum flexibility and avoid concentration risk, enterprises spread their applications across cloud providers. But this activity is not trivial as it would require honoring the constraints which the customer has, and at the same time generating the most optimal configuration of cloud resources. There are a few challenges associated with this. Firstly, the applications to be migrated need to be documented well, in order to migrate them successfully. Some applications may be very old (legacy) and need an architect overhaul which means the cloud feasibility needs to be checked. Also, enterprises would like to have an optimal list of cloud vendors that satisfy their need. To overcome these challenges, we propose a smart system for determining multi-cloud pathway for applications. The system identifies cloud feasible applications, understands their requirements and recommends optimal set of cloud vendors honoring their constraints. This is enabled through Reinforcement Learning with Human-in-the-Loop. We show our results with a use case from real world scenario.