I just did the beginning part of this back in December.
If you're in Norfolk, I would highly recommend spending the first day travelling to the Atlantic Yacht Basin. Leaving from there gives you a good starting point for making the locks and bridges. Be aware that the bridges are generally closed for rush hour on weekdays—6-8 AM—and you will need to plan for that. Leaving Norfolk on a Saturday will let you go through most of the bridges on the northern end of the ICW on Sunday, when the traffic closures will be less likely.
Stick to the center of the channel, as there are unmarked deadheads and stumps along the outer edges of the channel. Mast height should not be a problem, though draft is pretty deep for the ICW...which has shoaled quite a bit in many areas.
Going southeast to Pamlico sound and the Ocracoke inlet is one option. However, the fixed highway bridge (U.S. Routes 64 and 264) between Redstone Point on the mainland and Weir Point on Roanoke Island has a clearance of 45 feet, which will be a problem for you.
If you go east of Roanoke Island, you should be okay, provided you stay in the channel. Outside of the channel is way too shallow for your draft most of the time. However, this route in bad weather is not a good one, as it is very exposed and the channel is fairly narrow, leaving you little in the way of options.
I would recommend going the Alligator River-to-Pungo River route instead. This route has no height clearance issues for your boat and is much more protected than the Pamlico sound route. You have a lot of choices of marinas to stay at once you get to Belhaven. If you go and stay at the Oyster Creek Marina (#8 on the screenshot), you only have a 30 NM trip or so to Ocracoke Inlet, so you should be able to make the inlet before night fall fairly easily.
However, I would highly recommend not entering the Alligator River at night. The entrance channel is a dogleg and it is fairly shoaly. You should stick to the eastern side of the channel as much as possible, since the shoaling is worse on the western side. One good plan is to stay at the Alligator River Marina overnight. They have a depth of 7' IIRC, so you should be okay there. It is just north of the Alligator River swing bridge on the western bank of the Alligator River.