I have to run, but you should look for information here about Tampa, which might have Clearwater info. Look also for Salt Rock Grill ( a steak house), Keegan's and Frenchy's which are casual seafood and steak places in the beach in Clearwater/St. Pete. Tio Pepe in Clearwater is a very old fashioned Spanish restaurant somewhat like Colombia in Tampa, tho many prefer it. Look into Tarpon Spings, also. The Greekest place in the US. Well worth the detaur. Rusty Bellies is a day-boat fish place there, and any local can direct you to good Greek. Mr. Souvlaki is simple and excellent.
Are you looking to travel non-interstate highways between those places? Good luck; you'll need patience and a good radar detector, but it sounds cool.
Cedar Key is nirvana for oyster lovers. That's where they come in by the boatload. live it up.