Let's not get too excited. We're staying in Charleston until Feb 15 more-or-less. But. What's next?
What's next is to get further South. It's right cold in Charleston.
While the Sea Islands of South Carolina and Georgia call to us, it's winter. So we aren't listening to their call.
We're looking at the following legs for Phase III.
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Charleston to St. Marys. 163 nm 27h. Refuel. Charleston Harbor Marina
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St. Marys to Cape Canaveral. 170 nm 28h. Refuel. Port Consolidated Fuel Dock
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Cape Canaveral to Key Biscayne. ~144 nm ~24h. Refuel. Cape Marina.
These seem like prudent hops that don't require impossibly great weather windows.

Here's the sketch of the Charleston to St. Mary's leg.
It omits the hour and a half of navigating down the Cooper River and out of Charleston Harbor.
It also omits and hour or so of working our way up the Cumberland River behind Cumberland Island. It does, however, make sure we stay reasonably close to shore and avoid heavy ocean weather.
The ugly part of the overall plan is the Port Canaveral part. There's a bridge and a lock that need to be traversed to get to the handy anchorages.
The other possibility is to go in at Daytona and anchor near New Smyrna Beach. This is a nice spot we've used before. It may be slightly simpler to enter and exit. The problem is being located 6 hours further north. Instead of two 24h passages, it's an 18h passage and a 30h passage. Both are leave making depart-late-arrive-early kinds of passages.
I think we may break this into one short leg and one long leg. We have until mid February to finalize the trip, produce float plans, distribute them, and make sure we have provisions.