Mike...in three weeks do you plan to get to Charleston and back with those intermediate stops...or do you plan to leave the boat in Charleston and get it later?
You'll need 2 days to get to Oriental and Ocracoke...then you need to turn around and spend another two days to get to Beaufort (via Oriental)...
Assuming you wish to travel offshore rather than motor the ICW...you would then jump to Masonboro Inlet/Wrightsville Beach which is as close as your going to get to Wilmington unless you come in instead at Southport/Cape Fear Rive and motor way up river. The jump to Masonboro will be an overnighter BUT should only be attempted on a good forecast since it is NOT an all weather inlet and there is nowhere else to run in bad weather. My own preference would be to plan to do a longer jump to Southport/Cape Fear on a good forcast since that IS an all weather inlet. It can get quite rough...but will not get closed out. From Cape Fear, you can make Charleston directly in a day or two depending on the wind. Bailout inlets if bad weather is approaching are Little River in settled conditions and WinyahBay Georgetown which is an all weather inlet and a great place to visit anyway.
Here's the material I think you should get for the trip:
-Maptech Chart Kit Norfok to Florida...will give ICW and offshore charts needed.
-Dodge Guide to Southeast US inlets...don't even think about it without this!
- Skipper Bobs Guide to anchorages along the ICW...saves money and also provide shoaling info and bridge info.
- Doziers Mid Atlantic Cruising Guide will give you info on marina's, towns, boatyards, etc.
I would count on $1.50-$2.00 per foot per night plus electric for each night you spend in marinas. You'll need fuel to motor and charge your batteries up. Food will depend on your own tastes and how often you hit the restaurants vs. cook on the barbie or catch fish!
Take a multiple GPS's with you and plot waypoints for all the inlets and turns you want to make in ALL of them. Get your chartbook well in advance and plot and mark your intended courses and enter the waypoints so it is all in your head. Be sure to plot bail out waypoints & courses as well as the time to do that is NOT when the S*** is hitting the fan. Bring plenty of batteries.
You should have an EPIRB. a liferaft, a shortwave SSB portable radio to get weather forecasts in addition to normal equipment.
Take a the basic USCG sailing course if offered locally. You'll get stuff you already know but you will also get an excellent grounding in navigation basics, plotting, compass work etc.
I am looking at your trip as 7-8 days of sailing one way and assuming perfect weather and no down time for sightseeing. If you are looking to go there and back, I would suggest that it is doable but ambitious.
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