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Although my experience is limited, and I have not had to place a claim. But I have been using Jackline through the Gowrie Group as well. So far, great service, good policy coverage.
They have been very responsive and flexible with adjusting sailing areas.
Our contact: Rachel Sloan, Gowrie Group
Insurance continues to be an on going issue for many. I do have a bit of news, that for us was on the positive side.
We have used Markel's Jackline Policy, sold by the Gowrie Group in Annapolis, since the exit of Pantaneous USA from the market. It is expensive, but we have not found a lower cost policy that met our standards, and covered all of our needs.
One of the limitations of the Jackline policy was the southern edge of the Caribbean hurricane exclusion zone for the summer season was placed at 10º 50' North, just north of Trinidad. We wanted to base our boat out of Grenada for the summer, so we asked if they offered a rider to move the limit a bit north. The answer was "Yes." For a premium of about 10% over our normal annual premium, they would extend our coverage north to include our requested cruising zone. We took that offer.
Here is the part that might be of interest to a lot of people: The actual rider that we received not only included Grenada, but ALL of the Lesser Antilles. Everything in the eastern Caribbean from Venezuela, all the way up to, but not including, Puerto Rico. The catch is the underwriters have a maximum number of these riders they will write, in order to limit their total exposure to storm claims. We were told by the broker they usually get more requests for riders than they will write. I have no idea if they accept them on a first-come, first-served basis, or have other criteria they apply. But for people interested in summering in the eastern Caribbean, it might be a useful tool to explore.
The other moral of this story is if you have a special request, always ask. They just might say "Yes"!