I think that parts of the ICW are fine, but it is not sailing. Might be a good idea to stay inside to miss Hatteras - which means you get to do one of the nicer bits of the ICW. Other than that, just pick your spots. Lots of opportunities to sail. The Gulf Stream is a long way offshore most of the way down. Even off Florida you should have a couple of miles. As for eddies and the like, sometimes they will help and sometimes hinder - such is life. I think some of the posters need to get out sailing a bit more. Maybe it is a winter thing.
Heading back to Lake Ontario for this summer. Relatively few stops along the way from Grenada. Martinique, Guadeloupe, St. Martin (must have something to do with the French food), then Bermuda, New England and up the Hudson/Erie Canal. We were going to go via Newfoundland and Labrador but June remembered that one of the kids is getting married this summer - details, details!