This paper examines holistic education initiatives of two high-performing education systems--Finland and Singapore. This qualitative analysis captures a phenomenological schooling experience of holistic education under the two systems. Our conceptualization of holistic education focuses on two key dimensions: transformative learning and community engagement. Indications of transformative learning were observed through the (un)structured play activities that students engaged in. For community engagement, we examined the imperatives that underpin community engagement initiatives that students were exposed to. A sociological explanation of this account discusses the context that shapes approaches to holistic learning, and how changes in schooling approaches mirror-changing educational landscapes in both Finland and Singapore. Implications on Singapore's holistic education will then be drawn.