Naples: From Frontier Outpost to the Wealthiest Town on the Gulf

Naples, Florida is a city that named itself after Italy and then, over about a century and a half, made the comparison plausible. When a handful of Kentucky businessmen sailed down the Gulf coast in the eighteen eighties and found a bay they thought beautiful, one of them said it reminded him of the Bay of Naples. The name was adopted, a pier was built, a small hotel was opened, and the town was platted in eighteen eighty-seven on land that had been empty, at least to European eyes, for decades.

The Calusa people, who had built a sophisticated civilization along the southwest Florida coast for thousands of years before Spanish contact, were long gone by then, erased by disease and colonial disruption over the preceding century and a half. What the Kentucky businessmen found was pine flatlands, a wide Gulf beach, and air that in winter felt like a gift. What they built was modest.

For its first six decades Naples was a private winter retreat for a small circle of well-to-do families who came to fish and rest and did not particularly want company. There were no railroads and few roads. The six-hundred-foot pier that Walter Haldeman and Captain James Canty built in eighteen eighty-eight was the lifeline: supply boats tied up there, and visitors arrived by sea.

The town burned slowly through debt and difficulty, passed entirely into private hands, and remained a secret that few outside a tight social network knew about. Two things cracked the isolation open. The Tamiami Trail, the road slicing through the Everglades between Miami and Tampa, reached Naples in nineteen twenty-eight, the first land route of consequence.

Then came Barron Collier, the advertising tycoon who acquired more than a million acres of southwest Florida and, as part of his compact with the state, funded the completion of the Tamiami Trail in exchange for a new county named for himself. Collier County was created in nineteen twenty-three. The county seat sat for decades in Everglades City until Hurricane Donna destroyed that town in nineteen sixty, and the seat moved to Naples.

From that moment, Naples became the official center of a vast and rapidly developing county, and the transformation from secretive winter colony to one of the wealthiest cities in the United States accelerated in earnest.