Disclaimer I am not an insurance professional but I have had a few claims over 25 years of sailing and 3 boats. These were for big things. Lightning, Sandy, breaking the steering pedestal.
I assumed you checked your policy for the extent of coverage for sails and under what conditions they cover damage/replacement.
Also consider that some insurance companies are depreciating parts so you may not get full cost of a new sail even it they cover it. But you will have a claim.
I hear you about the small claim vs rate increase. And to that point when I switched from boat US I took a $1500 deductible.
I blew up a sail a couple years ago in a squall. It was a good sail, lightly used but old. I didn’t really think about an insurance claim, as the sail was old.
If your insurance is through an agent (I use Gowry), I think it is fair to ask questions about your policy and the coverage.
It’s just a gut feeling, but I would hope that they would be more responsive and honest as they should not be in the business of denying claims like the carriers are. I have experience through my boat club that our agent was great at answering questions about our policy along with the cost/benefit of insuring certain things.
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Happy Holidays to all- I would like to again draw on the experience of the group, this time about insurance. The basic question is when it is worth submitting an insurance claim. I know from car insurance that you don't want to submit relatively small value claims as they will raise your rates as a result. My small genoa was destroyed in a late season noreaster and needs to be replaced. A laminate racing sail is not cheap. I don't want to ask the insurance company so I wonder if anyone has experience with this issue. Dave