It disturbs me that you don't mention sails in your list of prep items. Having the right sails and knowing when and how to use them can make sailing the trip a breeze. Be prepared for sailing in winds from zero to 50 knots if you go offshore, don't expect to be able to motor in moderate to extreme conditions, save that for no wind. If solo plan days of 30 miles or less not as tiring on the ICW and their are plenty of great stopping and looking places. Offshore save inlets are usually more than 100 miles apart, 24 hours or sailing or more. Done any all nighters since college?
Important it is the trip not the destination or a schedule that is important, have fun, it in the attitude of everyday life.