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.
Back to Grenada in early December. Not sure I will remember how to sail. 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.