I guess I just wouldn't let a boat or any other deal go south because of something like this. I mean what does a boat insurance policy cost for the year... $500-$600? If you could get a 6 month policy or even pay by the month, it would be considerably less as most insurance companies, or at least mine, prorates their coverage. Even if you bought an insurance policy for say $200-$300 just for yourself being out on the water with the sea trial run, imo that's not worth potentially losing the boat over. And if you did go through with the purchase of the boat, you'd already be covered for the trip home, and could extend the coverage out for the entirety of the year, broaden the coverage, etc. As you mentioned before, if you're spending what I'm assuming must be at least $50k-$60k on a boat, why let the deal go south for a couple hundred dollar insurance policy? I know I wouldn't. Based off your comments above, it seems to me like you might very well be overthinking the entirety of this just a bit much, and/or maybe talking yourself out of the deal. Oh well, moving onward.