[CaptainMorgan21]

From your post, it sounds like you do not have the experience or knowledge to attempt this trip. Even going by way of the ditch can be very trying. If you do not have very good navigational skills, charts, and seamanship skills...I would suggest going with someone who has.

As far as what is the best time to go to Florida, from December to about May. Good luck!

 

[CaptainMorgan21]

From Chicago to New York you could go the Erie Canal to the Hudson River
instead of St. Lawrence Waterway. There is a lot of info on the Great Loop website. You would have to unstep your mast until Troy, NY. You would go by West Point, Governors Island, Statue of Liberty, and the Verrazano Bridge before having to go out into New York Harbor. A most beautiful trip. From New York Harbor is open ocean until Barnegat Inlet, where you could take the ICW. Or you could stay outside until Cape May, New Jersey. Good luck.