Dude, if you are looking to stage before heading to the Chesapeake here are some options in NE Florida. South to North.
Hammock Beach Resort. Good quality docks. A bit more expensive but you get the run of the resort with their free shuttle to then hotel, pools, beach on demand. They were pretty full then last time I spoke to the dock master.
Palm Coast Marina across the way. Older marina, but very functional. Very inexpensive, and nice people. Were were there the week before last for a mid-week cruise. Easy walk to the European Village for eateries. Nice walking and biking trails.
St Augustine Municipal. Refurbished after recent storms. Good marina with great staff. Current rips through there, especially at mid tide, but once you are tied up for the month who cares! Great access to down town and the restaurants and bars etc. We will be there in a couple of weeks for a couple of days.
Conch House and Camachee Cove marinas. Both good quality, but I would say Camanchee over Conch House. A bit of a walk into town though. Both have restaurants on site. Conch House can get a bit noisy - but that's because of the active Tiki Bar!
Further north in Jacksonville Beach you have Plam Cove Marina and Beach Marine across the AICW from each other. We stayed at PCM for 14 years with our last boat. Great people and easy walk to Publix and all other stores and eateries. Good boat yard there though they do not work on diesels. I would recommend PCM over Beach. Though Beach has access to a couple of restaurants.
Would NOT recommend River City Brewing downtown JAX. Not in great condition and the river rips through there.
Overall I would recommend Ortega Landing Marina. Great place, well maintained and protected, with good people. Walk to large mall with stores and restaurants. MTOA hold rendezvous there. Easy Uber to and from JAX airport. It is off the St Johns south of Jacksonville so a couple of hours down the river from the AICW crossing (maybe a bit longer in your boat) but I think still worth your looking at.
Finally, as I posted in another thread, Fernandina City Marina is now back open. That gets you further north for your jump northwards. I have not been there since the rebuild so cannot give any details on where they are at right now.
We have transient spaces at our marina, but we do not allow liveaboards - apart from a couple of nights when you first get here and a couple of nights when you get back and ready to set off. So that probably doesn't work for you.