Just got a quote from Progressive for a new Blade & trailer, $220. Over the phone, probably the easiest phone transaction I've ever made. May not even bother with more quotes!
That was my experience as well. Yes, they cover sails and racing. It also covers the boat while trailering. It is also a "replacement" policy and not an "agreed value" policy. I.E. if your boat is destroyed they pay out what it takes to replace the boat with same year or newer...whichever is available. Also to my surprise, I received a letter last fall saying that because I had not made a claim, my $500 deductable was just reduced by $125. It will continue to be reduced by $125 every year that I do not have a claim until it is at $0.
That being said, I've never made a claim on my policy, so I can't speak for what their response might be...hopefully it would be as sharp as their up front work.