I just PM'd
@caneinorlando, you should try some of the spots up on the north side of town. One of my brothers lives on the Wekiva, and a good spot to start from is Katie's Landing, which is about a mile north of his place. People go kayaking and paddleboarding through his backyard all the time, though less so now because a tree fell over the channel (and my brother refuses to chainsaw it out).
He also owns land around Wekiva Island, another good place to check out (though a gator bit a woman's arm off a couple of years ago, the facts are in dispute as to whether she provoked it, she was just past the Bridge to Nowhere over by Wekiva Island). We went up the St. Johns to Blue Spring this past weekend, but we also sometimes head east through Lake Monroe to the lesser known part of the St. Johns, over by Mullet Lake and Lake Harney.
I'm partial to the north side of Orlando, I canoed those rivers for years when I was in Boy Scouts.
Another one of my brothers lives over by Lake Jesup, not far from Black Hammock, but there are a TON of gators up that way.