Do I need to rent a car in Naples?

Usually not, and often you're better off without one. Naples is walkable in its old core around Fifth and Third, but golf, the beaches, and dinner are spread along the coast. A car and driver keeps a sunset-then-dinner evening easy.

Between Southwest Florida International Airport (RSW) and neighborhoods like Fifth Avenue South, Third Street South, Old Naples, the Beach, a private captain on call covers everything a rental would, minus the counter, the parking, and the return. You ride, someone else drives.