Do a search, it has been discussed before. In summary though, you absolutely need liability insurance at least. I think it is somewhat irresponsible to race without that in this day and age. As far as total coverage through ussailing or any other number of companies.. I think it is a good idea unless you sail a beater that ain't worth much. These boats cost 15k + and you could get stuck out in some serious stuff and get really screwed and you would be out most of that (some would likely be salvageable) if you had a total loss. I would definately get boat specific insurance, not rely on homeowners or car