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.
Back in the water in Grenada - with new main and #2 and cockpit canvas (Santa came early). 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.