The route people seem to take in these circumstances is:
Route. Via ICW & Outside (Beaufort/Morehead, NC)
140 nm, Annapolis, MD to Norfolk, VA
ICW 623 nm, Norfolk, VA to Beaufort/Morehead City, NC
497 Beaufort/Morehead City, NC to Stuart, FL
So around 1270 nm.
Anyway...any input from you knowledgeable folk would be appreciated, as trying to plan ahead of time. Thanks.
Easiest input = you mileage is wrong.
140 from Annapolis to Norfolk is about right.
Norfolk to Beaufort NC is more like 200 miles (Norfolk is Mile 0 on the ICW - Beaufort Mile 202)
Beaufort to Stuart is closer to 785 miles. Stuart is Mile 987 (you do the math . . .)
I disagree with Gary about jumping out at Norfolk.
Your opportunities to go outside are between Beaufort NC and Stuart. You can run overnight from Annapolis to Norfolk (20hours) but with a new boat and volunteer crew, you'll spend 4-5 days to get from Norfolk to Oriental. From there, you have a series of 12-36 hour coastal jumps that you can manage and extend if the weather allows.
I don't know about your details, but 40 miles a day is a reasonable average on the ICW. Not easy but doable. The location of anchorages and currents / tides play in here and there, but I don't think you are being unreasonable to figure 40 mi a day at this time of year. If you can work in a few offshore runs heading south from Beaufort, you can cut out huge chunks of time (i.e., Beaufort, Little River, Charleston, St Augustine).