This chapter explores the transformative power of philosophical wonder and its potential to foster a deeper connection with the world and the self. It examines the role of wonder in philosophical practice concerning figures such as Socrates, Kierkegaard, Heidegger, and Buber understood from an “apophatic” perspective. From this perspective, the chapter distinguishes between different forms of wonder, such as phenomenological wow-wonder, Socratic wisdom-wonder, and apophatic without-why-wonder. It argues that deep contemplative wonder is neither to be understood as feeling or cognition nor identified with the experience of the sublime or awe. Deep Contemplative Wonder is more to be understood as an ontological event and I-Thou-relation. The chapter also discusses how wonder can serve as an event and way of being for coping with life’s challenges, including grief and illness, and proposes the creation of “communities of wonder” to promote existential health. It also presents the “Wonder Compass” as a practical model for exploring wonder and as a way to promote deep wonder in everyday life and communities. It argues that philosophy achieves its transformative potential when it fosters a wondrous and caring relationship with nature and that cultivating wonder can inspire actions that are more in harmony with nature and promote a sustainable future.