Jerry,
We live in centrl FL and do most of our salt sailing on the east coast around Ponce Inlet. I'm not well versed in Penensacola weather, but I can generally say the Florida weather is weird in the winter. Cold, windy and choppy where you wouldn't want to be on the water. Then another front moves through and its' mid to upper 70's, nice wind and calm water for two weeks.
Look for the weather fronts and plan your visiits to arrive just before a good one.
Wish I could tell you more.