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Start with the boat in the driveway, on a trailer. Walk him around, &etc. It's actually best to start off with a smaller boat, on blocks in the yard. That way you don't have to lift him in. Let him get comfortable getting in and out of a boat that doesn't move or rock. When he's okay with that, do the same with a boat that's tied up to a dock. It's best if it is a calm day with no harbor traffic making wakes. When he's comfortable with that, idle the engine(s) without untying the boat. And keep going like that, adding elements of real boating, as tolerated, until the mad dog is riding a wakeboard.
 
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