The Northwestern Gulf Coast in Florida is some of the prettiest, varied and most interesting cruising territory in the US. Naples to Clearwater is cruising just off the coast where you see pretty highly developed property, Clearwater to Apalachicola (150 miles) (I think the distance to Panama City (190 miles) might stretch the range on a 460DA) puts you in what is called the Forgotten Coast. Apalach. is a cool, laid back locals town with great restaurants and some of the nicest folks on the planet. From there, run the ICW up to the Gulf Co Canal where there no development, but the ICW follows pristine natural creeks and rivers....it will be you and the alligators, egrets, herons, and eagles for 1/2 a day......... hang a left and go 5 miles to Port St. Joe which is in the pocket of St. Joe Bay. Next, run the outside in the Gulf past Mexico Beach, Tyndall AFB to Panama City/Panama City Beach. This is the home of some of the best skilled marine craftsmen and tradesmen as well as diesel service. There is enough maritime activity (bottom work, 6 travel lifts locally, electronics, canvas, upholstery, detailing, diesel service, and technicians very familiar with Sea Ray boats) here that prices are kept very reasonable by the competition. If you have a punch list from your survey or just your wish list, you could do a lot worse than leaving the boat in a transient slip in Panama City Beach for a while to get the things done you might have a problem getting handled at home.
Then, from Panama City, you need to look at your weather window because you can choose to go on the outside or via the ICW. The ICW takes longer and this part of it isn't nearly as interesting or picturesque at the Apalachicola part. Plus, Panama City is a major shipping port so there is a decent amount of barge traffic and narrow land cuts. From Panama City westward to Pensacola, I have passed 6-8 tows in 8 hours but on other trips, have not passed another boat of any kind. The trip over to Pensacola is one where you pick you route and live with it, at least 1/2 way, because the only pass to get from the Gulf to the ICW is in Destin, 45 miles West of Panama City. The water from Port St. Joe west to Dauphin Island is almost as pretty as the keys and the beaches are the white sugar sand you see in the tourist rags and are unparalleled.
Honestly, I think the trip from Naples to Dauphin Island isn't one to hurry thru just to relocate a boat. On this part of it you will experience about everything and every boating condition possible, except for passage thru a lock.........and that interesting, but you can live without it. It will be a great learning experience and a very enjoyable trip all rolled up into one. Dont pay a hired gun to have that fun..................do it yourself!