I know where you are coming from, and in my case, I hope I have not waited too long. I hope to celebrate my 72nd birthday while cruising down the ICW to the Florida Keys next October. I've lived an exciting life, done just about everything a person could ever dream of doing, but I've never made this trip aboard a sailboat. I'll be cruising for 7 months, most of the time by myself (no crew) on a 33 Morgan Out Island. From the Keys I hope to head to the Dry Tortugas, then over to the Bahamas before heading back north to the Chesapeake Bay's upper reaches.
Good Luck, and I sincerely hope you find the means to make your fantastic voyage in the not too distant future.