you REALLY should insure your boat - at least liability and ESPECIALLY if you race it (even once a year). It's cheap (my 2004 Nacra F18 costs $181 / year for FULL coverage including sails and the trailer).

I was involved in an incident a couple of years ago that totalled a Hobie 18 and my Nacra 6.0NA...I certainly don't want to run the risk of paying for that out of pocket (just imagine if anyone gets hurt!).