Like Gettinthere,
I draw 5'-7" w/filled tanks & people onboard. I've sailed inside & out from The Panhandle to Miami over the years. This has taken me in & out of the more shallower channels but for the most part, most are passable. I'm not crazy going to Tarpon Springs.
The ICW runs well from Clearwater to Charlotte Harbor. South of here, there is one area called The Miserable Mile with tricky currents & skinny water. Going south, I generally pop out from South Seas resort marina thru a small pass on the north tip of Captiva Island. Have not used this in several years so check with them first. I've never gone to Naples, but the local guys can help you with specifics.
I do like what Sumner says about a wing keel. Steadier & less roll in seas than a fin keel. Some like a modified keel with less draft. You can run aground anywhere man, a smaller draft only means you go aground in shallower water. It's important to stay between the poles. that's all. On the left coast of Florida, personally, I wouldn't more than a 5'-6" draft.
CR