I encourage you to read Don Casey''s "Sensible Cruising" book. Besides lots of great tips from a reasonable, non-extreme man (there are so many extremists among cruisers), and the last section is a fictional first cruise for a couple going down the ICW to the Bahamas. It details highs, lows, and lessons learned.
I left in my mid-30''s, and everyone I met said the same thing, "I wish we''d done it when we were young like you are." I never once met anyone who said "I wish we had waited..."