If you read my post on "What's Your Biggest Bone-Head Move Sailing?" you will see that I almost deterred my 6 year old from ever sailing again, due to an out of control heel!
He has since accepted that Dad will never let that happen again and is back to looking forward to our sails.
Even at his age we get the "When are we going back?" question out of boredom, not fear! So, we try to make him a big part of each outing.
First of all, he has his own "Pre-Sail" checklist and I let him go around and check all the rigging, safety items, etc... itís very funny because he often reminds me of things Iíve forgotten (such as tying the jib sheets!)
Once under sail we give him the tiller (ready to help if necessary), or ask him to "adjust" the jib sheets.
We get out the binoculars and point out items of interest for him to look at on the water as well as the shore, he ALWAYS looks forward to lunch, sometimes we drop the sails and fish, and his favorite activity is to drop the sails and swim off the back of the boat using a dock line to hold onto and, of course, wearing our life vests. Mom usually stays at the tiller just in case.
Sometimes we let him bring a friend, or cousin and he seems much more eager to stay out. As a last resort, we bring his DVD player or PSP (charge Ďem up at home or in the car, sailboat batteries donít last long powering these things!) and he can go down into the cabin with them and relax, or even nap!
We found that the swimming really does the trick though!