This one isn't related to the islands but is still a good sailing tale nonetheless. And it comes with a video bonus!

Basically though, some friends and I were sailing in Northern Michigan and we swamped a 24' Pearson Ensign. We had to float to shore, radio for help and then be towed back to base... Several broken phones and some scared women later we made it home, got the boat back above the waterline by stuffing children's lifejackets underneath the bench seats, bailed her out and she was good as new with a fresh wash to boot!

Video here: Swamping a 24' Sailboat