I didn't wakeboard it... and I don't remember exactly what we did..... But I live in St.Pete/Tampa... we went south, then took a left and got on the okechobee* water way, then crossed lake okechobee**, then took someotehr waterway, and popped out on the east coast.
I WOULD NOT WAKEBOARD IT..... I think throughout hte whole trip, we saw like 300 alligators... we counted!!
For just a trip it was awesome... there are lots of hotels along the way. Again I wouldn't wakeboard it. One reason is there are a lot of LOCKS and damns, and another reason is the gators. O and a large portion is idle speed.