I did sail my boat from LI to Florida back in 2008 and had good crew.
Sailing in Charlotte Harbor is pretty good most of the year and yes we get real hot and less winds
during summer months maybe June July August and it' our rainy season with thunder storms hit and miss but if you have easy quick trip out to Harbor many go in late after noon or when weather looks good for some sailing.
The first 2 years had the boat in Burnt Store was good with quick in and out of Marina,I do go back to LI during July August and part of Sept to visit with lots of family & Mom & friends so don' t do any sailing but start sailing pretty fast in Oct.
Nick