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.
Finished the circumnavigation in early February in Grenada. Have to work on a book project for the next several months so the boat will be waiting for next year.