What are you planting it in? If you want to control the water it gets then what I do is plant them in soil that drains well but holds moisture.
Like Fox farm soil mixed 7 parts soil 3 parts perlite and with about 2 inches of loose black cinder on the bottom of a five gallon bucket. That will keep it from getting to wet when it rains but it will also keep base moisture in the soil for any dry spells. however planting outside you don't really know what your gonna get. You have to rely on mother nature to get her to the finish.
I grew outdoors in Hawaii, but you can do it there on accident. Just flick a seed off the porch into the grass when your rolling a joint and a few weeks later you see a plant growing outta nowhere. FL should be a great place to grow outdoors, the climate should be pretty good for it.
As far as when to plant, you should wait till after the last frost of winter. Yeah you don't get frost i know, so in your case i would plant anytime after march first, longest day of the year is june 21st so thats when the days will start to shorten again. Harvest outdoors will be near october.