First up, lets be absolutely clear your goals because your plan does not fit one.
You absolutely mean "The Caribbean" to mean the Bahamas?
Lets ensure you know. Look it up in Google. Then use the correct terms.
If your goal is the Caribbean
you want to leave from Beaufort North Carolina, especially on a smaller boat.
If you want to go to the Bahamas
you want to leave from Ft Lauderdale.
I have sailed from the Bahamas to the Caribbean and it isn't an easy trip... and took as long as the nice gentle trip from North Carolina.
If you are going to the Bahamas then your plan to go down the ICW is fine. Its an easy motor the whole way. You do about 50 nms per day. All hand steering.
All your dates are far to late for me. Even northern Florida is very cold in November. But you are from the north so your cold might more fridged than I like.
I feel its safer to be south of the Chesapeake by October 1st because of equinoxial storms. The old adage was go immediately after the Annapolis Boat Show... but then they moved the boat show 2 weeks later.
1) Lake Huron -> Erie Canal = Depart mid August, go as quick as you can to be in Norfolk by 25 September (If you want a more relaxed time schedule go now.)
3) ICW -> Head south from Norfolk = October 1st
4) Florida -> Bahamas = 1st December
5) Cruise Caribbean = December through May.
Best places along the route to spend a few days: NYC (79th St Boat Basin); Norfolk Virginia; Beaufort North Carolina; Charleston South Carolina; Savannah, Georgia (18 miles up the river but worth it, park on the town dock on the riverside in the centre of town); St Augustine, northern Florida.
I found that the winter came down from the north at greater than the 50nms I could motor down the ICW... and when the fog lays in on that narrow, winding, shallow trench it can be quite difficult