Any recommendations for trip insurance that protects your investment in a charter should a hurricane ruin a planned trip?

Your charter company should have some recommendations.
I have used World Nomads in the past.
They paid off when we canceled a BVI trip due to covid.

Please click on the link here for Insure my Trip. This will give you a broad range of insurance plans, and you can compare them side by side, to see which one best fits your needs. If you click on the link here, your cost is the same, but TTOL gets a small commission.

We’re big fans of a few insurers, Allianz being our top recommendation. We’ve filed several trip interruption claims with them over the years and all have been handled promptly. We’ve also had two medical emergencies while traveling internationally - both including hospital stays - and the rep took over both cases immediately, refunding our initial out-of-pocket expenses within hours or a couple days. So customer service is important in an emergency, and they have been there for us. We’ve also had good luck with Trawick (Nationwide). MedJet and GeoBlue are popular plans for their medivac policies…

Primary medical and medivac coverage is also critical in the event of a medical emergency. We look for at least $50k medical/$1 million medivac limits/pp. Good medivac coverage is important even in the Caribbean.

Also be aware that not all top insurers/ insurance policies are contained within the insuremytrip catalog. For example we used insuremytrip to compare policies several years ago but our go-to insurers no longer shows in the results for some reason. So broad research is key.

We’ve never included the cancel for any reason (CFAR) coverage because it is more a luxury than a necessity. But some plans offer that if you want to spend the $$$. And most policies stipulate coverage for pre-existing conditions (PEC) only if you purchase the policy within a 10-day or other time frame from when booking your trip.

Good luck!

And of course most travel insurance plans do cover trip cancellation for named storms as long as they are named after you purchase the policy. Not sure what the specific charter outfit’s cancellation policy is due to named or unnamed storms…