Hey finally a topic I know a little about. Caladesi by airboat very doable. Have done it in the past, lots of people come over and talk to you. It is an awesome island, entry day fee is $4 and the docks are new floating aluminum. There is a snack bar with hot dogs, etc.. no alcohol allowed off the docks, although not enforced if you act accordingly. Short walk to the beach which is very nice, outdoor showers indoor bathroom/changing rooms. I would launch from sunset beach in tarpon springs. boat ramp is just sandy area, utilized by waverrunner/bayboats/airboats, head due west to three rooker islands, run shoreline on the inside (depending on weather) or outside south too caladesi. this is not the closest boat ramp but very nice ride. You are also close to anclote which I run the a/b up several bars to pick up refreshments etc.. and you can go fairly far east past us 19 on the a/b. restricitions are no a/b after 11pm. If you are just looking for a nice island to hang out and party, three rooker bars are nicer than caladesi for hanging out at. plus lots of things too look at if you catch the drift. The water from sunset beach to the icw is grass flat and shallow. crossing the icw be careful heavy boat traffic etc...Have a good time it is really nice. For reference sunset beach is the road south of howard park which is also a neat county park with a natural boat launch area which is not as good as sunset's. hope this helps.