Damn, that eliminates Grouper Creek and Dusenbury Creek and the run across the bay.

I am thinking of setting up and staying at Gilbert's and tearing down at Caribbean Club. Would that be a possibility?

Launching at Caribbean would mean doing Grouper, Dusenbury and Angelfish creeks before you even get to the starting line. That is about 10 miles, if the wind is light or current running the wrong way, could be a long morning.