Not only that but where are you leaving the 'East Coast' from? Its a big coast.
Fair question. Here's our "story." First, we're years out on this, but in light of the time of year, it's fun to start dreaming and planning.
We're looking at either a full school year (September through August) trip, or one that is only half a school year but 8 calendar months (January through August). If we do the latter, we would run the boat down to Florida in the fall, fly down at the end of the year, and start our cruise from there in January. In this scenario, we'd skip the ICW on the way down, of course, and consider it for the trip back. If we do the full year, we'd do the ICW on the way down. We have two young boys who will be a little older by the time we go, but still kids to be sure.
I think we likely would want to avoid long ocean passages, as I just don't think my wife and one of my boys would enjoy it. That sort of knocks out the Carib 1500, unless I get crew to sail the boat and they fly to meet me (sort of goes against the point of this trip). Which leaves the Thorny Path, if we choose to go to the Carib.
And that's really the heart of the question. We are going to do the Bahamas, because we really want to. So, with an 8-month window starting in FL in Jan. and needing to end up back in NY (and get far enough north before hurricane season) do we go past G-Town, or not? My inclination is not, and that has been our thinking up until now, but I just had lunch yesterday with a friend who recently did a similar trip (he continued on east across the Atlantic), and he's encouraging me to go to the Carib because he thinks we'll be bored if we stay just in the Bahamas. I don't agree with him about the "bored" part, but he did put a bug in my ear about trying to make it to the Carribbean.