Coverage & Claims
The simple is, yes, you will have to file 2 claims. The damage to your boat would have to be claimed on your boat insurance policy.
The answer will depend on the coverage you currently have on your policy. There are two instances where boat insurance would cover an injury to a passenger caused from falling overboard.
While your homeowners policy can extend to boats, it only offers coverage if they are on your property and is normally limited to a dollar amount well below your boat's value. This also doesn't consider the liability that you encounter every time you use your boat.