Frequent hurricanes affect agricultural productivity, food security, economic security, and human wellbeing in the Caribbean islands. We assessed recent hurricane effects on the agricultural sector, and the challenges faced by farmers, foresters, and advisors related to hurricane preparedness and recovery in Puerto Rico and US Virgin Islands (USVI). We used qualitative and quantitative survey methods to compile perspectives from agricultural advisors related to hurricane effects on farmlands, preparedness and recovery measures taken by land managers, and the needs regarding preparing for and responding to future hurricanes. Survey responses from over 200 advisors at eight institutions provided insight into the most devastating hurricane effects across farmlands, including issues related to power outages, communication, road access, and fallen trees. Our results highlight strategies considered critical for hurricane preparedness and recovery but not prevalent in application among land managers. Advisors' perceptions suggested that farmers and ranchers apply essential recovery practices, but critical short-term preparedness practices are limited, and long-term preparedness practices are uncommon. Advisors also indicated the need for more training and educational resources to improve hurricane recovery response. We conclude that better planning to minimize the vulnerability to future hurricanes can be achieved through an increased understanding of how preparedness and recovery practices help mitigate hurricane effects, improved interagency coordination for hurricane response and preparedness, and integrated educational campaigns with advisors and land managers.