Re: AAA type service that will also tow the boat home?
Short answer is some boat towing insurance extends to the trailer but read the details to be sure.
I have AAA and when my car broke down, they would not send someone to "tow" both. First, I don't think anyone, legally or sensibly, would tow a car while it's hooked to a boat (three unit road train). I wanted to put the car on the rollback and the boat on the trailer hitch of the roll back. No doing.
But if you think about it, what roll-backs have a rear bumper, much less a hitch, at boat trailer level?
So I was faced with hiring the tow truck for two trips--one for the car and come back for the boat--the car being covered and the boat being my cost. I was doing a 50 mile tow including across the Chesapeake Bay Bridge Tunnel, so that would have been big bucks.
So I just did what every good boy in trouble does--called my mom to come get me!
(OK I sent the car home on the rollback; she came in the stawag and, even though she's pulled plenty of boats, I drove it, us and the boat home).
In a similar situation (I'm not saying "next time" out loud, and she is "no longer available") I'd pay the tow truck to take the boat a short distance to safe storage then come back and haul the car. That or prevail on a friend or relation to come with a second vehicle. Another reason to be nice to people.