When we were able to slow down and hang out for a few days or a week, we enjoyed ourselves the most. If I did the ICW again, I'd try to break it into a series of areas to slow down along to break the monotony of the daily 40-50 mile days.

In Toms tris case, I think a trailer able boat would be a perfect option for the Bahamas. Once you get there(Bahamas), it didn't seem we needed as much boat. Weather is greAt, you're outdoors or in the cockpit almost all the time. A trailer able tri would give you a world of shallow gunk holing and anchoring, all to yourself. It's a lot cheaper way to go too.