Re: ? Sail from Lake Erie to Florida late August
I would not say that the Hudson is spectacular but it is a very nice trip as is the Canal itself. To the OP, any of the Landfalls would be fine for the St Lawrence route as long as you have radar. If the idea is to go down and come back then it makes sense to go down the St Lawrence route and come back via the Erie. This way means you avoid coming against the current which is doable but very slow.
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!