In recent years, music aficionados have increasingly been consuming music via public music streaming platforms. Due to the size of the collections provided, music recommender systems have become a vital component as these aim to provide recommendations that match the user’s current context as, throughout the day, users listen to music in numerous different contexts and situations. In this paper, we propose a multi-context-aware track recommender system that jointly exploits information about the current situation and musical preferences of users. To jointly model users by their situational and musical preferences, we cluster users based on their situational features and similarly, cluster music tracks based on their content features. Our experiments show that by relying on Factorization Machines for the computation of recommendations, the proposed approach allows to successfully leverage interaction effects between listening histories, situational and track content information, substantially outperforming a set of baseline recommenders.