From someone who sails off the beach in Daytona I think the surf the most fun and the lack of it the one thing that is missing from the west coast. Nothing beats double trapped surfing the swell in ocean ocean. Closest thing to flying without the parachute.
But the real question is the time of year and the sailing skills you have. If are going this time of year I reccommend the Keys. Great place called Rock Reef Resort on Key largo. Bay side so the wind is a little better behaved that the ocean this time of year. They have a small beach and are cat friendly. Great islands to sail around and bays to explore and some of the best water every. Another great place in the keys that is cat friendly is the Islander on Islamarada. Large setup area and sailing to the reefs offshore. But it is ocean side. If you are going in the summer I reccommend the east coast because there is no or little wind on the west coast. Fall and spring head for the west coast of south because the surf can be a little unpredictable north of West Palm Beach. Dunedin is a great place to sail but you may find it a little expensive around the easter break and there is no where to stay and park the boat at the hotel. They allow some overnight parking at the causeway but you need to check with the local on permits. Many of the beaches around Clearwater will not let you launch off the beach so be careful of where you stay. Same problem with Sannibel and Captiva. I will let the panhandle folks speak for themselves.