re: Clearwater, FL shore/bay fishing

Go check out the Gandy bridge, between st Pete and Tampa. I had luck a couple of times fishing there when I lived there, and I have a buddy who still goes there. You want to park on the same side as the marine reserve base but the lot past the cell tower right by the bay (if you drive by it will make sense, and if you want more info I can mark up a google earth screen grab at the office in the morning) walk to the area sort of
Under the bridge and cast out a little to where the old bridge was (not sure if anything is still there as they demo'd that Bridge recently)

Or rent a kayak at weedon island preserve and go fish back there. It's a nice little state park.