can't comment on the legal perspective, but I'd be SURE to know where are we going, what's the route, and if there are any bridges or other known hazards. Whether or not he asked my draft I'd volunteer both air and water draft, and in my case, would also mention the 28ft beam.
When anyone does anything on my boat I make it my business to tell them about anything I can think of that's unique and could cause a problem if he didn't know.