Hi DDW,
...just about every other time has been after the holidays, so I don't see much problem with your schedule.. (grin)
Obviously, the weather dictates everything at that time, but I've had some great trips south in January... And if you're stuck running the Ditch, it's my favorite time of the year to do so, really nice to have it to yourself... I'd say the ICW is more do-able than you think, there aren't many spots where your draft will really be a problem... The Wilkerson Bridge could be dicey, I'd figure a way to heel your boat thru there if necessary, but chances are you'll make it... You could go around thru Pamlico Sound, but going around the top of Roanoke Island might be a bit close with your draft, but again I think you'd be fine... With a good window, you can go out around Hatteras of course, but you'd be missing what I think is one of the nicest sections of the ICW, and the best chance of being able to sail on the inside...
As Jim mentioned above, Claiborne Young's site I think is the best resource for current conditions on the waterway... Check the status of the work being done on the fixed bridge at Snow's Cut below Wrightsville, you might need to go out around Cape Fear...
Charleston is a stop everyone seems to love, it's a very nice town, and a great spot to take a break, and the City Marina is one of the nicer stops on the trip...
Dave discusses the straight shot from Hatteras to the Bahamas, I've never actually done that... Not sure I'd be all that inclined to do so in January, unless the weather was looking very favorable... One of the reasons being, I question to a certain extent the point of getting into the Bahamas too early in the winter anyway... My last few trips south, the weather was cold and windy down there until mid-February or so, and when I eventually got over there, most everyone was telling me I hadn't missed much...
Many people make the mistake of heading for the Abacos first, as well, where it's likely to remain colder, later... If you did sail straight down outside, I'd recommend keep on going past the Abacos, Eleuthera and Cat, maybe checking in at a place like Clarencetown, or Georgetown, then working your way back up from there... That way, you could be far enough south to escape the full brunt of some of the fronts rolling thru earlier in the winter...
But in general, just going down the coast can be a really nice trip, plenty of wonderful stops... the routine I got into my last few trips seemed to be to hang for awhile in Lauderdale, and then Miami Beach - a spot I've really come to like - do one final big provisioning, and then head over after the Boat Show/President's Day...
Good luck, hope you're able to make it this year, you're gonna love the Bahamas, even with your draft... (grin)
best regards,
Jon