Augmented reality (AR) technology is gaining popularity and scholarly interest in the rehabilitation sector because of the possibility to generate controlled, user-specific environmental and perceptual stimuli which motivate the patient, while still preserving the possibility to interact with the real environment and other subjects, including the rehabilitation specialist. The paper presents the first wearable AR application for shoulder rehabilitation, based on Microsoft HoloLens, with real-time markerless tracking of the user’s hand. Potentialities and current limits of commercial head-mounted displays (HMDs) are described for the target medical field, and details of the proposed application are reported. A serious game was designed starting from the analysis of a traditional rehabilitation exercise, taking into account HoloLens specifications to maximize user comfort during the AR rehabilitation session. The AR application implemented consistently meets the recommended target frame rate for immersive applications with HoloLens device: 60 fps. Moreover, the ergonomics and the motivational value of the proposed application were positively evaluated by a group of five rehabilitation specialists and 20 healthy subjects. Even if a larger study, including real patients, is necessary for a clinical validation of the proposed application, the results obtained encourage further investigations and the integration of additional technical features for the proposed AR application.