The benefits of regular physical activity for individuals with disabilities (IWDs) are well recognized. Nonetheless, IWDs report several barriers to physical activity participation, including limited access to qualified and experienced personal trainers. Limited research exists from personal trainers' perspective. This qualitative study aimed to examine the experiences of personal trainers who successfully improve the fitness of IWDs. Individual interviews were conducted with ten personal trainers, focusing on educational and occupational background, experiences training IWDs, and experiences training IWDs within gyms. Thematic analysis produced five themes: (1) personal trainers working with IWDs need specialized education and extensive, often multidisciplinary, experience; (2) personal trainers are most successful when they have the opportunity to work with IWDs who have a diverse range of disabilities and differing expressions of each; (3) a robust network between personal trainers and allied healthcare providers is necessary to support IWDs; (4) access to physical activity is enhanced when trainers manage resources appropriately; and (5) personal trainers can empower IWDs to be advocates for their physical activity needs. Future research could examine the effects of an adaptive hands-on educational intervention among personal trainers to enhance IWDs' health and fitness.