Health disparities among Native Hawaiian kupuna (elders) continues to be a major health issue. The purpose of this study was to explore the meanings, experiences and perceptions of care of Native Hawaiian kupuna in Hawaii who live with chronic illness. A qualitative design was used with in-depth interviews conducted with 15 Native Hawaiian kupuna and five Native Hawaiian health care providers. Study themes that emerged were the importance of knowing and respecting the Hawaiian culture, the difficulties of living in two worlds, knowing how to speak from the heart, and the need to learn from each other. Findings revealed that integrating knowledge and understanding of Hawaiian cultural values and perspectives are essential in designing culturally competent approaches that promote the health and well-being of Native Hawaiian kupuna with chronic illnesses.