If you want to see ALL of Florida...then Tiger Point Marina in Fernandina is a great place to drop her in:
Fernandina is a nice town but even more important is that Cumberland Island is just across the St. Mary's River into GA and that is so spectacular it should not be missed. Since you have the time, I would also suggest making the 50 mile crossing to the Bahamas rather than cruise FL for months. Much nicer...and a whole different world and an easy trip if you wait for good weather in W. Palm Beach prior to crossing.
Imagine is right about Green Cove Springs too and Jacksonville is a great city to stop at if you have a few days to venture off the ICW.
Other must see's are St. Augustine (try Oyster Creek Marina if you don't anchor out). Vero Beach is also a good stop...with town moorings and free transportation everywhere in town for re-stocking or anything else you need. After that...there's not much for the sailboater till you get to the keys except for the nightlife in Miami/Ft. Lauderdale. Have fun!