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.
Heading back to Lake Ontario for this summer. Relatively few stops along the way from Grenada. Martinique, Guadeloupe, St. Martin (must have something to do with the French food), then Bermuda, New England and up the Hudson/Erie Canal. We were going to go via Newfoundland and Labrador but June remembered that one of the kids is getting married this summer - details, details!