Let me first address the "why" part of your question, as the "how" will be a little more complex. Most human migration, especially prior to the Modern period, was driven by a need or desire for resources. Even well into the Modern period, First Nations people (like the indigenous Taino and Arawak) lived highly mobile lifestyles driven by access to seasonal resources. So, why did indigenous Caribbeans migrate there? For access to food and other resources! As I mentioned, the "how" is a little more tricky. We do not have historical records detailing the peopling of the Americas and must rely on archaeological materials and "best guesses." Archaeological evidence indicates that people were living in Trinidad at least eight thousand years ago , and by seven thousand years ago were continually pushing north towards Cuba. Based on this evidence, we could infer that once groups of people had arrived in South America, they began pushing northward into th...