This chapter seeks to contribute to a better understanding of the variety and spatial unevenness of sustainability transitions by studying Chorotega’s regional transition from livestock farming to tourism, a process that has unfolded for over four decades. We argue that agency has been mobilised across actors in multiple scales. The national government and supranational organisations initiated the transformation through policies aligning economic growth with environmental conservation, while regional and local actors, including businesses and educational institutions, have been crucial to adapt the changes. To analyse the interplay of agency at various scales, the study employs sustainability transitions and economic geography frameworks to identify how macro- and micro-level agencies influenced the initiation, evolution, and establishment of an industry that has prompted a sustainability transition in the region. Despite the green and sustainable image of Costa Rica, this chapter highlights the contradictions and limitations that sustainability transitions can face. Indeed, economic vulnerability, social inequalities, and environmental challenges persist, suggesting a need for a vision that centres around environmental and social challenges.