I worked as an unlicensed captain for nearly 20 years before I stepped up and "got licensed." Insurance companies at that time approved me without question as it was all based on experience.
Just remember, a piece of paper does not a captain make. I know licensed captains that I wouldn't let park my Corvette.
If you are running your family 60' or less yacht as owner/operator, then I wouldn't sweat it. You can take a US Power Squadron or USCGAux boating safety course and get the same discount on your boat insurance than if you were licensed. In fact, I teach owners and have my letter of completion accept by underwriters.
If you are not "taking passengers for hire" e.g. charter, then contact you marine underwriter and see what their criteria is. If you are not satisfied with their answer, call another one.
