Rick:
I have done that trip 3-4 times. You can anchor out or stay at marinas or a combination. Here are the stops (well not all, just the ones I can remember) that I made heading north the last time.
Titusville- Anchor in front of the Municipal Marina
Daytona Beach- Drop your anchor in wide, deep spot just off the ICW
St Augustine- The old anchorage area is now a mooring field. Pick one up
Cumberland Island- Anchor across from the NPS dock and dinghy dock. I spent a few days biking through the park. seeing the ruined mansion, the wild horses and secluded dunes and beach.
Georgia- Other than Cumberland Island, I hate Georgia. Mostly desolate marsh grass and zig zagging back and forth. If the weather is right, go outside at Brunswick and reenter at Callibogue Sound S of HH.
Hilton Head- Anchor in Broad Creek but it is pretty packed with moored boats. N of Skull Creek marina is another anchorage but I haven't used it.
Beaufort, SC- Anchor just south of the City Marina. Use the large dinghy dock and go ashore for great walking through the historical district plus decent restaurants (or dock your Tug along side for the day, but you must move it at night)
Charleston, SC- Just west of the city before the bridge is a little oxbow that can accomodate 2-3 boats. But if you are going to stay at a marina anywhere, this is the place so you can check out the city.
Georgetown- Anchor or ask a local if there is a free mooring available.
Barefoot Landing- It is kitchy but I always stop at this little marina along side the ICW in Myrtle Beach, wander the shops and have dinner at one of the theme restaurants.
Mile Hammock Bay- A Marine Corps facility but boaters are (mostly) welcome to anchor but not go ashore
Swansboro- An alternative if MHB is closed
Wrightsville Beach- The anchorage is about a half mile E of the ICW, and is open to the south, but has great facilities accessable from the dinghy dock in the NE corner.
Beaufort, NC- Taylor Creek is full of moorings, so go N through the lift bridge and anchor in Town Creek south of the airport.
Oriental, NC- Snag one of the two Town Dock spots (someday we will have more free town dockage if the politics can be settled) or anchor behind the breakwater before the marina.
And you are home.
It is a great trip that can be done in a couple of weeks or take another week and smell the roses along the way.
David