Speak to BobtheBuilder about the trip to KW. He does it all the time and can give you a few pointers.
As for slips for the week you are in town; Naples city docks are fixed height and not all that convenient from Pelican Bay. I would look at a transient dock at Pelican Isle Yacht Club in north Naples; a one week rental at the Collier County park / ramp at Wiggins Pass; or, a wet or dry slip at Naples Harbor Yacth Club by the airport. Pelican Isle and Wiggins pass will be the most convenient to Pelican Bay.
There's certainly a wealth of places to go by boat from Sanibel and Captiva to Marco Island.