Sounds like an epic trip!
Since you are in Miami...head down to Key Biscayne, Crandon Park, perfect spot to learn kitesurfing.
Wind forecast looks good the next days and get lessons.
You want already to be kiting going onto the trip, and not loose time
Maybe see you next week at Crandon!
And pls add new spots and picture to the kite spot database on www.splocs.com
during your trip!