In recent years, personalized learning has become a buzzword in the field of education and an approach that schools across the United States have adopted in their attempts to account for the diverse interests, aspirations, and needs of their students. Despite the growing interest in personalized learning, there is a dearth of empirical research on this educational approach, particularly as it relates to the student experience. Given the paucity of research in this area, little is known about the extent to which personalized learning can offer students a more beneficial quality of experience than traditional educational methods. This question is further complicated by the fact that personalized learning has been defined and put into practice in diverse ways. Given these conditions, the purpose of this study was to explore students’ experiences with more humanistic forms of personalized learning at three high schools in Vermont. A pragmatic approach to qualitative research was used along with self-determination theory (SDT) as a framework to investigate students’ perceptions of their autonomy, competence, relatedness, motivation, and well-being within the context of personalized learning. SDT was used as framework because it offers a lens for analyzing how social contexts affect people’s experiences and proposes that individuals experience higher qualities of motivation, engagement, and performance when their basic psychological needs for autonomy, competence, and relatedness are met. Study findings, which are based on interviews with 28 students from three Vermont high schools, suggest participants generally felt autonomous, competent, and related in their personalized learning environments, which contributed to their intrinsic motivation, engagement, and well-being within these settings. Some features of personalized learning that supported multiple facets of students’ basic psychological needs were the individualized nature of instruction, student-driven curriculum, and structures that enabled and supported community-based learning. Although many students suggested personalized learning supported their basic psychological needs, some struggled to direct and manage their own learning, which diminished their feelings of competence while others indicated that the individualized nature of their projects undermined their sense of relatedness to their peers. Overall, the findings indicate that humanistic approaches to personalized learning have the potential to contribute to a more beneficial quality of experience for high school students than traditional educational methods. The study has implications for educational policy and practice as it suggests personalization may be an effective approach for engaging a variety of students with their education and promoting the skills and dispositions for lifelong learning.