Waste management in the small island communities of the Maldives is challenging due to the fragility of the low-lying islands and the logistical complexities of a geographically dispersed setting. The Soneva Namoona team is developing a holistic sustainable waste management model that is suited to the context of such islands. In this article, we present the findings of household-level waste segregation trials implemented in four islands in Baa Atoll using the Trials of Improved Practices (TIPs) research method. Thirty-eight of 45 households successfully completed the trial, and we observed participants’ high willingness to segregate. The main challenges included difficulty in communicating and coordinating new segregation behaviors with household members and the lack of space in households for keeping separate containers. We also observed that coordination with the Island Waste and Resource Management Centres (IWRMCs) was vital for successful household segregation.