Welcome Pamther (love it). Yes
on the Master Gardener festival, you will be able to buy good plants that are suited to your area there, and also get lots and lots of good advice. Most Master Gardener programs in Florida have a help desk or plant clinic that you can contact by phone or e-mail with questions, too.
Annuals do well here in the winter, but they really do poop out by June, when our all-day and all-night heat sets in. So in the fall its fun to plant some annuals for the cooler weather months - I highly recommend things like Nasturtiums planted in October. If you plant them now, you won't get great mileage from them. Go for some flowering perennials like various Salvias and maybe Pentas. They will be beautiful, drought and heat tolerant and even attract butterflies and hummingbirds if you're lucky.
A picture of the area where you want to plant would be a big help in giving you advice. Um, have you considered that pots might be stolen if they are out near the street? (sorry to float this negative thought, but . . . been there, had that happen) If you can sink the pots into the ground a bit, and mulch over the edges so the pots don't show, that might make it not so obvious to light-fingered folks. This method really works well for a garden in pots.