Best sailing is in spring and fall, but summer sailing can be good too. I have a generator and run it whenver away from the dock so the cabin is either warm or cool. We have a full enclousure that we keep on until mid May and put back on in mid October. With the enclosure, I can sail in pretty cool weather and be comfortable. One March, 30 knot winds out of the the NW, 40 degrees and sunny with the enclosure on I sailed 42 miles one day from Lighthouse Landing to Cypress Bay. April and May are also great months some years and some years they are wet. June is good and up until mid July it can be good. From Mid July until late in August the humidity and heat can be tough. We don't sail much during that period. September, October and early November are good. October is great, crisp, very little rain and usually good winds.
Even in Florida, it is hot and humid during the summer and early fall. The most miserable sail I ever had was from Punta Gorda to Key West in late September. Humidity and heat were awful - couldn't wait until dark and it got worse!
Find a weekend and come down to Lighthouse Landing and rent a cabin. They will rent you a 26 foot Colgate and you can give it a try!