Research reveals little about how rural micro firms learn as they collaborate for tourism development. Drawing from Lave and Wenger’s (1991) community of practice perspective, this chapter explores the elements related to micro-firm community learning and presents the findings of an interpretivist multi-case study of two evolving learning communities (ELC) engaged in rural tourism development in Wales and Canada. The literature review reveals catalyst, structure, strategy and boundary as elements which impact sustained learning in this setting. Empirical findings demonstrate that learner autonomy is challenging in both cases while the literary identified elements shaped learning relationships differently in each case. An ELC model adapted from prior research (Reinl and Kelliher, 2014) is presented. Progressive brokerage is emphasised as a fundamental competence for sustainable learning in this environment. Calling for a sustainable learning orientation, recommendations are offered to optimise ELC support and avenues for future research are outlined.