If they do not ask, I did not think you had to tell. I was in Ins for over 20 years on the other side of the coin.  If it does not ask on the application normally you would be OK. Have things changed? I was a Branch manager for Transamerica Occidental. I did not mean to conceal, just answer what is asked by agent and application. Many cos will not insure if liveaboard, but if you have a legitimate address other than the boat there is no limitation on how many days you can stay on it. In the south they would be bound as the questions were properly asked but up North who knows. Allstate agent told me the same thing as did Statefarm and Nationwide.