From Fishing Colony to Florida's Wealthiest City

For the first seventy years of its existence, Naples was kept small by design and by geography. Walter Haldeman, the Louisville newspaper publisher who helped found the town in eighteen eighty-six, ran it as a private winter preserve for a circle of Kentucky and Ohio families who came to fish and rest and did not particularly seek growth. Roads were poor, a railroad did not reach Naples until nineteen twenty-seven, and the town's inaccessibility served as a natural filter.

The Tamiami Trail arrived in nineteen twenty-eight and cracked the isolation open. Then came Hurricane Donna in nineteen sixty, which badly damaged Everglades City, and in nineteen sixty-two the county seat moved north to East Naples. These events put Naples on a different trajectory.

Wealthy retirees and second-home buyers, discovering that Naples offered what a lot of Florida did not, specifically a relatively uncrowded beach, a preserved downtown of low buildings and shaded streets, excellent fishing, and an exclusivity that felt earned rather than manufactured, began arriving in larger numbers through the nineteen sixties and seventies. The development of gated golf communities and luxury residential subdivisions in the surrounding county brought wealth at a scale the original founders could not have imagined. By the early twenty-first century, Collier County had become one of the wealthiest counties in the United States by per capita income.

Naples had traveled the complete arc from frontier outpost where supply boats docked at a wooden pier to the address of choice for the American wealthy, a journey that took less than a century and a half and involved two founders, a hurricane, and an advertising magnate who needed a county named after himself.