Jamaica’s Nearest Caribbean Neighbours Here is a map of the Caribbean. If you examine it closely you will be able to see that the closest countries to us are: Cuba (90 mile north of Jamaica); Haiti (120 miles coast to coast); and the Cayman Islands (270 miles coast to coast)…. Register Login Contact us RelatedPEP Practice National HeroesThe National Fruit, AckeeGrade 4 Social Studies Quiz — Sept. 4 2015You are doing well. Tell your friend, it is so good!