Better make it $250 per boat and factor in the cost of additional insurance for the vehicle and cargo. Then calculate the taxes that that you'll pay to each state you drive through hauling freight. Then you'll need to consider Homeland Security mandated drug testing and background check for the driver, which if you ignore it and get caught is a felony with a nasty fine and jail time, not to mention confiscation of the vehicle and cargo.

My wife and her brothers own a truck line. Overall, being in the transportaiton and logistics business is a nightmare and is only getting worse. And you wonder why a loaf of bread costs almost $4. It's probably better to just find another sailor heading to the same event and split the cost of gas.