I've had my catamaran's insured thru State Farm Insurance since 1980 or so.
My premium's started out at about $47 per year for a Hobie 18.
Last year I think my premium was appx. $147 on my 2004 H-18 with 9K of coverage, and $247 on my 1986 H-18 with 5K of coverage.
The agent explains the higher premium on the older boat with less coverage as a function of their loss experience. Over the 28 years, I have had 3 or 4 claims, only one was "race related" they have paid every claim with out a problem.

My boat policies all specifically state they do not cover the boat in a race, "except sailboats".

If the agent you are dealing with does not write sailboat inusrance very often, he may not be familiar with the language in his own companies policy.
I had a new agent tell me my boat would not be covered in a race and when I showed him the language in my policy, he was stunned. Felt kinda nice to teach the agent something about his own companies coverages.