Having just read information on different types of airspace in Florida, in class C D E and G airspace you are actually allowed to fly above the cloud by 1000 feet
If I'm not much mistaken (it happens occasionally
) the departure and destination airfields have to be VFR and with FEW or SCT clouds. If you want to fly
through clouds you will need a full Instrument rating.
VFR OTT is a separate rating in Canada but with the same criteria.
rgds
CB