I reside just north of Orlando. Some of us leave our boats mast up on the beach all summer(just get it off before hurricane season), but you might not want to do that with a N20.
Are you just a racer or do you also recreation sail?
With so many great places to sail within a few hours drive time you may just want to keep the boat at home then pick the place with the best conditions for the weekend.
During the winter months it's the west cost or Kelly Park or the Keys. There are some good weekends for the ocean but not many.
The best regattas down here seem to happen during Fall and Spring(with the exception of Tradewinds in January). More than enough to keep you on the road during any free weekend.
In the summer the only place to have wind is the ocean(although Ding says there is never enough). The fleet in Cocoa Beach is very active. Several active groups in Tampa(Gulfport, Tampa Bay Catamaran Assoc.) The best social sailing fun group has to be Dunedin. Daytona puts on several races each year.
Another option if you want mast up storage or just need a place to get a sailing fix in every once in a while check out the Halifax Sailing Center in Daytona. Best deal going.