Homeowners is easiest
I have my O'Day 23 as a seperate policy with the same agent that does my autos, home and other sailboat. I have liability and stated values for the motor, trailer and and hull. If the boat sinks they bring it back up for me. If the boat breaks loose and sinks a nicer more expensive boat they handle that too. I sail on a small mid-western lake and its pretty cheap for me to insure. I checked and they said I could sail anywhere as long as I don't go more than 75 miles off shore. At hull speed it would take almost dawn to dusk to go that far in my little boat. If I go 75 miles away from land on my boat I don't think I'll be planning on coming back to file a claim.