I've raced mono's out of the Clearwater Club, very nice facility and location, Gulf on one side, small bay on the other, so no matter how windy it gets you can still sail inside if it's too rough outside.
Dundedin is the finish line for the Macho Man, did that once, nice sandy beaches but you must be carful coming in through all the sand bars. Get your boards up or die.
I spent most of my time on the east coast though and on the lakes.