A growing population of adults over 65 means communities in the United States must prepare to address the unique transportation and health needs of older adults. Phase I of this study sought to determine whether a community-based “buddy” program that pairs college-age students with transportation-disadvantaged older adults could improve quality of life for seniors in Hillsborough County, Florida. A multidisciplinary approach that included transportation planning, public health, and instructional technology was adopted to assess current barriers and identify opportunities for intervention. Specifically, the project conducted an assessment of transportation and health resources in Hillsborough County, and compiled existing community resources that could benefit older adults. Using this data, the Healthy Buddy website was created and pilot-tested in interviews with older adults in Hillsborough County. The interview population was also asked about their individual health and transportation needs, as well as their openness to participating in the Healthy Buddy Program. From these qualitative interviews, it was determined that there is a need to improve the mobility and independence of older adults in Hillsborough County through the provision of information on existing transportation and health resources. Furthermore, the interview population was receptive to the Healthy Buddy concept, and felt it could improve their transportation access and quality of life. Overall, the interview results obtained in Phase I conveyed a need to improve transportation access and health information access in older adults, and as such, will inform the continued development and implementation of the Healthy Buddy Program in Phase II of the project.