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.
In South Africa doing lots of boat stuff. Departure north from Cape Town around December 15th. Arrival in the Caribbean around the beginning of February, after 5300 miles or so.