Need to find somewhere that takes winter liveaboards
I think that the climate conditions in Kingston are doable and it is a lovely place to live, but you need to have a marina that operates in the winter and I doubt that either of the two large ones in Kingston do (downtown and Collins Bay). I know of several marinas in Toronto that have significant winter populations (Bluffers, west side of main harbour (forget the name) and Port Credit). Now is a good time to check on availability since the one downtown at least has a waiting list.
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!