Years ago a hurricane filled in the inlet joining Caladesi Island with Clearwater Beach, and so you have to drag, carry, or bring your wheels to tote your boat around 100 yards in distance.
The mangrove tunnels are a wonder to see and go through, rising from old oyster beds, these trees are neat to see with the way the roots are coming out of the water and with the canopy closed overhead so that you can't see the sky.
Suggestion: you might bring two paddles for this trip - a less expensive paddle to use in the tunnels and your regular paddle for when in the open water, you could be pushing off the sides of the tunnels as well as there is vegetation that could occasionally catch a paddle.)
For information about the island : http://floridastateparks.org/caladesiisland/default.cfm
Generally we try and go from the causeway to the tunnels and then across the sand to the gulf side (weather permitting) and then travel just out of the surf along the beach back to the inlet and then back to where we started.
Tidal influences here really impact the enjoyment of going through the tunnels - when at low tide many of the tunnels are impassible in a kayak/canoe without portaging. So plan your trip around High Tide: for the Denedin, St Joseph Sound area. Both of these tidal websites are good to use: http://www.softseas.net/ or http://www.saltwatertides.com/dynamic.dir/floridagulfsites.html