Check with IMIS in Annapolis about their Jackline policy for cruisers. The insurance company is Merkel Insurance. We have not had a claim with them so can't talk about that aspect but their coverage is good and not out of line for price. They understand the needs of cruisers.
Back to Grenada in early December. Not sure I will remember how to sail. Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.