The issue is how long you use your boat in each state. You may be required to have more than one registration. Here is the Maryland requirement:
If your vessel was purchased elsewhere or previously registered in another jurisdiction, is now in Maryland waters, and will use Maryland waters more than any other single jurisdiction during the calendar year, you are liable for vessel excise tax and must register the vessel within 30 days of entering Maryland waters.
If your vessel is duly registered in another jurisdiction but remains in Maryland waters more than 90 days in a calendar year, you may be liable for vessel excise tax unless you can prove principal use in another jurisdiction.
What is "principal use?" 8-701 of the State Boat Act
“State of principal use” means the jurisdiction on whose waters a vessel is used or to be used most during a calendar year, which is the period from January 1 through December 31.
“Use” means to operate, navigate, or employ a vessel. A vessel is in use whenever it is upon the water, whether it is moving, anchored, or tied up to any manner of dock or buoy. A vessel is also in use if it is kept in any structure in readiness for use.
Now, as you go down the coast, each state has it's on rules. If you stay in them long enough you could end up with three or four registrations. I'd just look at each state's requirements.
It's your choice of what to do. But you'd have a difficult time for this year convincing Maryland that they aren't the state of principal use.
My understanding is that Virginia's rule is also 90 days but they don't require registering documented vessels. North Carolina requires registration at 90 days. South Carolina only requires 60 days. Georgia also is at 60 days.
Now I can't tell you how closely or when other states will check you or do anything. But theoretically you could be required to register now in Maryland, spend from October to January in Virginia and register, spend January to April in NC and register. May and June in SC and register. July and August in Georgia and register and keep your documentation and FL registration the entire time. The safest thing is to leave each state before the time, even if it's just to come back.