Or is it 2 steps forward and one step back. hard to know as the up and down battle continues. Boat purchase price agreed on, check. Lining up the workers, check. Getting boat insurance, uh oh… Given my less than perfect motor vehicle record, the new boat owner syndrome, age of the boat and pirates of the Caribbean the seemingly simple task of acquiring boat insurance is fast becoming a monumental hurdle. Who wouldn’t want to insure 3 young men who have never done a trip to the Caribbean before, now come on!!!! Well, the good news is there are many insurers out there, but with the trip fast approaching and precious time being spent on this task, the window of opportunity is quickly becoming tighter and tighter.