I think I was one of the first PPRuNers to go to Naples, and very good it is, too. I hoped I might get an FAA IR - Naples delivered that and an unrestricted FAA PPL. I'm in California at the mo enjoying them!
The Wellesley is good value; the student accommodation I know nowt about.
We hired a car to get from Miami to Naples and from the Wellesley to the airport each day. It would have been very difficult otherwise. I doubt if there are viable direct flight options.