Transportation is a necessity in adult life. Qualitative literature regarding the usability of transportation to travel freely within the community (e.g., school, work, leisure activities) is widely circulated; however, information regarding transportation needs and barriers specifically faced by individuals with an intellectual and developmental disabilities (IDD) is limited. This study discusses the accessibility and usability of transportation avenues for individuals with IDD. Young adults with IDD (n = 9) explored their transportation experiences of accessing specialized public transportation (paratransit), ride-share, and personal vehicles independently. Researchers used a multiple-case study design to analyze interviews, observations, and document reviews. Results indicated the importance of teaching, maintaining, and generalizing transportation skills. Limitations and implications for research and practice are discussed.