The purpose of this study was to investigate why some Hawaiian language and culture-based (HLCB) educators perceived the Montessori approach to be congruent with their goals and values and to determine the salient features of the Montessori approach used by HLCB teachers who received Montessori training. The sociocultural perspective on learning provided the theoretical foundations and grounded theory methodology guided the research process. Interviews and focus group discussions were conducted with 40 HLCB participants, including 15 key informants who had at least 180 hours of Montessori training. Data also included classroom and school visits and analyses of school documents. Data analysis revealed six themes and two linkages that related the themes and their elements. Four themes were related to why HLCB educators have perceived the Montessori approach to be congruent with their values and goals. These were (a) similar views regarding their work as a lifestyle, (b) common pedagogical practices, (c) shared values and beliefs as educators, and (d) an overlapping world-view. One theme described the distinctions between the approaches. The final theme included challenges to implementing and maintaining HLCB programs. The findings suggest that researchers and teacher educators interested in culturally congruent education should take into account the underlying world-view of both the research paradigm and the participants involved, and that school reform should be comprehensive, culturally congruent, and generated from within communities and other stakeholders. They also indicate that culturally congruent, place-based education may enhance academic self-efficacy and could serve as a bridge between seemingly disparate educational approaches.