Despite the current technological advancement in agriculture to improve the production capacity and livelihood of the estimated 608 million smallholder family farmers across the globe, there is a need to uptake these technologies among smallholder farmers. The need for improvement exists due to their socioeconomic, governance, and environmental challenges. Additionally, a lack of adequate land tenure, financial inputs, and mechanical equipment restrict smallholders’ capability to apply new technologies. The Caribbean Community (CARICOM) has addressed the challenges of tackling poverty, water, and agriculture by incorporating climate-smart technology into the agricultural systems. CARICOM’s regional agricultural policy emphasized the importance of drainage and water management technologies to combat and address the challenges of saltwater intrusion, flooding, and drought. The combined systems include green engineering, agroecological practices, and natural crop protection to address these dominant factors in building climatic resilience. This chapter addresses the fact that integrating nature-based solutions in smallholder farming could be a source of conservation and safety of the environment, as well as social and economic activities. An empirical case study of a smallholder family in Trinidad and Tobago presented nature-based farming methods in soil and water management, integrated pest management, weed control practices, and seed storage. The results demonstrated a reduction in cost, improved genetic diversity of seeds, and cultivated plants, and helped to tackle poverty and increase sustainable food production (SDGs 1 and 2).