The Cayman Islands Customs website states: Duty Free articles are the following: Wood pencils, pencil cases, crayons, rulers, erasers, glue sticks, crafting glues, pocket folders, scientific calculators, geometry/compass sets, dry erase markers, pencil sharpeners (non-electric) and lunch containers. School uniforms (including uniforms for Physical Education and sports), school bags (excluding laptop bags), ordered and imported by Parent/Teacher Associations (PTAs), Home/School Associations (HSAs), and schools approved by the Chief Education Officer Homeschools are "schools approved by the Chief Education Officer" and therefore are allowed to bring in school items duty free. You will however need to show your homeschool approval certificate to the customs agent.