Having sailed out of the Islander for the 2004 Tybee 500, I can attest that it is a nice spot to rig boats etc. The launching area is quite shallow and you will likely have to walk your boat out beyond the pier and the race course will need to be pretty far out to get away from coral heads. While I wouldn't mind it, some might be concerned that the water could be considerably choppier / wavy on the Atlantic side of the Keys too. I also wonder how many of us Tradewinds sailors would support the Islander at $150 to $170 / night? How many rooms does Gilbert's have? I know they were fully booked at ... what was it ... $129/night? Maybe it's doable.