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 liability
from the vehicle you were driving is actually what will pay out for the other party's damage, and not the boat insurance liability, since the boat was out of the water at the time of the accident. Luckily, you will only have to pay a collision deductible
for your boat since liability coverage is not subject to a deductible.