Cleo - My nearly 8 yo son has plenty of experience in the Caribbean (and boats), but only on land-based trips. We've waited until now to take him on a sailing trip in order to feel confident about his ability to handle himself on the water (strong, confident swimmer) and on a serious sailing trip (ie: quasi open water). I'd love to have any suggestions/thoughts you might offer. The one thing I'm really hoping to do is to find other boat-based playmates along the way - I suspect that we will even though our trip is May - June when many kids are still in school (unless full time live-aboards).