Itinerary advice for going from Lake Michigan to Bahamas

[nuru05]

So we are new liveaboards and are planning on leaving in the spring from Chicago to ultimately end up in the Bahamas. We have considered a number of different options but are unsure exactly which one would be the best. The one catch is that we need to find 3 months between october and the following June to come back and work. So my questions to you guys would be

Is the ICW better than the mississippi route? We are leaning towards the ICW but are willing to hear opinions otherwise

When is the best time to head down the ICW? Conventional wisdom says after hurricane season, but would heading down right away in the spring and being in Florida by mid July and maybe heading over into Texas or something for the summer be a bad idea?

If heading down very early is not a good idea I was thinking we would start down the ICW in late september early october and take our time. We would probably take a month or so to get down the ICW. Which means we would hit Florida around early Novermber and head back to work for Novermber, December, and January. Then get back on the boat in February and head to the Bahamas for the remainder of the season.


Like I said I don't really know where to start and how to plan this. This first year will be kind of different because we are fighting winter up here. After this first year we will be able to work during hurricane season and leave our boat in the south caribbean.