This study presents an alternative process for designing and manufacturing customized trays for dental-whitening treatments. The process is based on a digitized approach consisting of three main stages: design of a reference model, its manufacturing by AM, and thermoforming of the tray. The aim of the study was to develop a high-performance tray, able to guarantee comfort, safety, and efficacy for whitening treatments. To evaluate the patient’s experience, some tests under real operating conditions were performed. Twenty people carried out a nighttime treatment of 14 days. Each patient was asked to assess the overall level of satisfaction and the comfort of the tray and its ability to retain the gel. Tooth whitening was also determined according to the VITAPAN scale. All patients involved in the study were satisfied and provided positive feedback about comfort and tightness of the tray. At the end of the treatment, 15 out of 20 patients achieved shade A1 on the VITAPAN scale. The mean improvement in color shades was about 7. These results confirmed the great potential of the proposed dental tray. Its use was proven to guarantee a high level of quality, flexibility, and customization of dental-whitening treatments, improving comfort, safety, and efficacy.