Transitional care programs are effective for improving patient outcomes upon discharge from acute care services and reducing the burden of healthcare costs; however, little is known about the types of transitional care programs for older adults across Canada. This exploratory study gathered an in-depth understanding of Canadian transitional care programs and described how each program functions to support older adults and family/friend caregivers. Nine key informants were interviewed about the development of transitional care programs within four Canadian provincial regions including Atlantic, Central, Prairie, and West Coast. Key facilitators and barriers influencing the development and long-term success of transitional care programs included program scope, program structure, continuity of care, funding, and health system infrastructure. Future research is required to identify how a broad range of transitional care programs operate and to disseminate knowledge with health leaders and decision-makers to ensure transitional care programs are embedded as essential health system services.