Context.After the fall of the Soviet Union, Cuba was plunged into an economic crisis with devastating effects on the agricultural system. With few options, the government restructured its agricultural system from an industrial model to a model based on smallholders and agroecology. After several decades, the results of this transition have been far reaching.Objectives.This research aims to elucidate some of the social, economic and ecological dynamics of this process. In so doing, it produces a more holistic and multi-dimensional perspective of how these changes have transformed landscapes and livelihoods in rural Cuba.Methods.To accomplish this, this paper presents a case study of a smallholder community which has undergone a shift from industrial sugarcane to small-scale agroecology. This research makes use of mixed methods, including remote sensing analysis, semi-structured interviews and archival work to understand how these this shift has changed landscapes and livelihoods in the region.Results. The result of this work reveals that while agricultural extent has plummeted, the production of staple crops has increased dramatically. This increased production has been accompanied by a doubling of food markets. Additionally, on-farm incomes have risen steadily. At the same time, strong environmental protections have greatly improved forest cover in the region. Together, these results demonstrate the process of replacing an extractive agricultural economy with one based on smallholder livelihoods.Conclusions. In the context of strong social, economic and environmental protections, such a transition can produce a number of concurrent benefits, leading to more multifunctional landscapes capable supporting livelihoods alongside ecological recovery.