My father has someone interested in his 40ft custom sportfisherman. This guys is extremely wealthy... has a 120ft yacht and is currently building his upgrade to 180ft.
He is also picking up a 63 Merrit next month.
He is also knows the builder of my dads boat... that is the contact.

He is thinking of having my fathers boat as his tender/fishingboat.

The guy wants to come charter his boat for the day w/ his own captain to see if he likes it.

How much would you charge for this charter???

big insurance problem there

How about considering it a test drive w/ a deposit.

Take him for a ride.

As long as the owner / insured is on board, anyone should be legit to drive the boat (at 40 ft).

If he wants to charge $$, make the test driver bring the beer or buy lunch.

He's no con man... our contact did a cross atlantic last spring w/ him on the 120.

I don't think a ride will do it... do not want to put off this guy in anyway... he is the only real prospective buyer... that can afford it.

And if the guy actually stole it.... we'd be better off...

I'd have something drawn up that he assumes all liability for the boat while he has it then. If he wants the boat without your supervision, that's the only safe thing. He can afford it.

If he disappears with the boat, as you said, you are fine then too. If he makes it back with it damaged, well, you have your liability letter he signed with him responsible to fix it.

Agree on a set amount that it would cost for a mutually agreed upon mechanic to go over the boat. Make this the amount of the 'charter'. That way, you can have the boat gone over with this money, to make sure there is no damage, and he can neglect to have this 'once-over' done if he agrees to buy the boat.