Did that route
(everglades part) in a 18 ft sharpie alone in 2001 but not during the race.
In the glades there is a fair amount of sailing with an easterly component from the trades and often narrow passages between the connecting bays with dense vegetation nearby blocking the wind
......so bring paddles.
Contact the Everglades park service
and get their camping guide ,bring water
,water and more water
. This is serious sh!t ;DO NOT wing it! Saw many huge gators , I would not go in water above ankles and the is almost no dry land ,mostly impenetrable mangrove with mosquitoes.
I don't know how rigged the race rules are now,but would consider staying in the Gulf a long as possible before diving
into the Glades where a sailing boat will have better wind
I do not consider it necessary to have "off shore" experience for the gulf legs,much of which can be sailed in water of a few fathoms;but you should be quite experienced (wilderness) camping on your craft and on some of the beaches along the gulf.
Do your homework,ck you tube, blogs,etc. so you will have a realistic evaluation of what you will be confronting.
The rangers told me that I was the first that they knew of to do the Everglades alone in a sailboat. (draft 9" board up)....but back then there were a few areas where the mast
needed to be lowered to clear overhanging vines and it was otherwise no particularly epic feat.
If you search this site you should come across where I have written more
............luv you all..............mike.......................