Periodically an event like this is held on Great Lakes, called the "Smuggler's Run." It usually goes off pretty well. You might want to consider trying again.
As to how it's managed when all the boats run at the same speed? On GL the way it's done is to follow a set route and arrange for various forms of monitoring/progress checking to ensure the rouge is being followed. So ultimately it's a test of the captains' navigation skills.