I'm afraid I'd take the safe and boring route. I'd set myself up as an alternate shipping method that avoids taxation. I'd sail into my clients depot, "Plunder" the goods we agreed to ship in advace as well as the hard currency that is my payday for the job. Take my "spoils" to the agreed shippind drop off point and sell my "stolen" goods to him for the remainder of my pay or a dollar if they paid up front when I plundered the originating supply depot.
Less people hunting me down that way,
Yup, most boring pirate ever! That's me