The purpose of this research is to explore and interrogate dynamics involved with positive health and transformation of urban Māori whānau and the challenges of pursuing this using the medium of wānanga. The research component of this thesis rest around a recent series of whānau wānanga held and embarked on in partnership with my whānau through a journey of re-connecting back to our whakapapa, marae and our culture. Current statistics for Māori reflect health and well-being as a site of continuous struggle and one where much work is necessary to ensure equitable outcomes for Māori. While equitable outcomes are an ‘in the future’ dream what remains is asking what steps do we have to take as a whānau? What is the Māori culture that we must capture, know, and strive for, in our whānau journey of self-discovery? The theoretical framework guiding this thesis is that of Kaupapa Māori. Within Kaupapa Māori theory acknowledgement and recognition of the effects of colonisation, destruction of culture and power imbalances are known as a given, with no need to question the validity of whether or not these are true accounts. A comprehensive literature review covering wānanga, Māori culture, Māori health & well-being, sustainability and more is included in this study. In terms of the research component, five significant themes have been sourced from a series of semi-structured interviews to best represent the experiences of my whānau members pertaining to connection to whakapapa; te reo Māori; tikanga Māori and marae. They are as follows: structural inequality; influences on Māori identity; cultural confidence; whānau capacities; and resistive strategies. Results identified spaces of progress and spaces that needed strengthening in relation to whānau building cultural confidence and connection to a Māori identity. In conclusion, this thesis ascertains a need for whānau to foster appreciation for lifelong learning and a compassionate approach for those teaching as key markers for nurturing and reconnecting urban Māori whānau to their cultural roots.