daniel - I live 2 minute away from winter park over in college park.
There is lake Eustis that hosts the wildcat regatta, and tons of regattas over on the Indian river/Banana River. I keep the 20 on the trailer and mostly do regattas that I can drive to and come home at the end of the day, which fortunately is quite a few.
The drive to New Smyrna is about an hour and you can drive and launch right on the beach there.