Can you sail a boat from Lake Michigan to Florida?

Answer 1

yes.

One would sail from Lake Huron, through Lake St. Clair, past Detroit and into Lake Erie. After sailing the length of Lake Erie, one would turn left at Buffalo and use the Welland Canal to go around Niagara falls to Lake Ontario.

Sailing northeast to Oswego, New York one can enter the New York State Canal System. A sail boat, however, must be un-masted and motor the canal system. The canals go from Oswego to Albany and the Mohawk River and to Troy and the Hudson River.

Once on the Hudson, the sailboat could be re-masted. From there, one would sail south on Hudson River to New York City, exit the harbor, and turn south to Florida.

This shortcut through New York saves a "boat load" of time. If you remember, this was the whole point of the "Erie Canal". Otherwise, once on Lake Ontario, the boat would have to sail the length of the St. Lawrence seaway, around New Brunswick, Nova Scotia, and Maine. That's a lot of sailing.

Answer 2

Sure ... you will most likely find it advantageous to use the Panama Canal during your voyage.