This is exactly what I will be doing if my numbers ever hit!! Though mine will be a close replica of the ship design of The Wicked Wench... Aka the Black Pearl... All automated to be crewed by a minimum of 3 or 4...
Head south from FLA island hopping then to panama canal then due west... doubtful Hawaii would ever be a stop, but Tahiti and Fiji are definitely on the list before heading north west for Asia...
Sounds great!