When Hurricanes Irma and Maria swept across the Caribbean in September 2017, they caused catastrophic damage to social and ecological landscapes alike, denuding Puerto Rico’s forests and decimating farms at a time of deep economic depression on the island. It has been estimated that 80% of agricultural crops were lost during Hurricane Maria, effectively wiping out the agriculture sector. Meanwhile, over the past 30 years, neighboring Cuba has developed meticulous agroecological systems that are reported to be more resilient to hurricanes, which Puerto Rico may benefit from adopting more prevalently. Maria has thus created an opening to rethink land use practices in terms of resistance and resilience against increasingly intense and frequent hurricanes. This research addresses this hypothesis, through a comparative study between Cuba and Puerto Rico’s ecological and social preparedness, response, and agricultural recoveries from recent hurricane impacts. The data comes from interviews with representatives from government, NGOs, and academics as well as farmers on both islands. The intention is to inform Puerto Rico’s recovery effort and strategy for agriculture development on a very urbanized yet highly forested island that must adapt to rapid changes in current economic and climatic instability while conserving forests and promoting food sovereignty.