Landscape stewardship is increasingly understood within the framing of complex social-ecological systems. To consider the implications of this, we focus on one of the key characteristics of complex social-ecological systems: they are relationally constituted, meaning that system characteristics emerge out of dynamic relations between system components. We focus on multi-actor collaboration as a key form of relationality in landscapes, seeking a more textured understanding of the social relations between landscape actors. We draw on a set of ‘gardening tools’ to analyse the boundary-crossing work of multi-actor collaboration. These tools comprise three key concepts: relational expertise, common knowledge, and relational agency. We apply the tools to two cases of landscape stewardship in South Africa: the Langkloof Region and the Tsitsa River catchment. These landscapes are characterised by economically, socio-culturally, and politically diverse groups of actors. Our analysis reveals that history and context strongly influence relational processes, that boundary-crossing work is indeed difficult, and that doing boundary-crossing work in smaller pockets within a landscape is helpful. The tools also helped to identify three key social-relational practices which lend a new perspective on boundary-crossing work: 1. belonging while differing, 2. growing together by interacting regularly and building common knowledge, and 3. learning and adapting together with humility and empathy.