Climate Change presents similar challenges to farmers, ranchers, and foresters in Cuba, Puerto Rico, and across the Caribbean Islands. With similar climates, crops, producer demographics, and climate change vulnerabilities, there is much to gain from sharing information and building collaborative partnerships. Already, the effects of climate change and its impacts on working lands are evident across the region. In 2015, a prolonged drought in Puerto Rico led to a reduction in crop yields, losses of livestock, and water rationing for hundreds of thousands of residents, highlighting how vulnerabilities within the region’s water systems can affect the ability of producers to respond and adapt to changing climate patterns. In 2017 Hurricanes Irma and María hit Puerto Rico with category 4 and 5 intensity and had devastating effects on agriculture and forests. In Cuba, there is evidence that the effects of climate change are already stressing the nations water supply, increasing erosion rates, decreasing crop yields, increasing the proliferation of vectors that cause disease, and contributing to a reduction in forest coverage. Climate adaptation for tropical island nations and territories is a daunting challenge. Cuba has had unique experiences that can provide important lessons for many of its Caribbean neighbors. Both Cuba and Puerto Rico have much to gain from sharing expertise in the realms of climate science development and dissemination to help both islands achieve a higher level of food security and climate change resiliency.