Naples.

Naples never had a first act as anything else. In the 1880s, a group of promoters led by Walter Haldeman, publisher of the Louisville Courier-Journal, bought the land and platted a winter resort, naming it for the Italian bay it was advertised to surpass. Their first piece of infrastructure, before roads reached this far down the peninsula, was the Naples Pier, built in 1888 as the town's front door: guests, freight, and mail all arrived over the Gulf. The town grew up behind it, cottage by cottage, along what is now Old Naples.

The man who connected Naples to everything else was Barron Gift Collier, the advertising magnate who bought more than a million acres of Southwest Florida in the 1920s and bankrolled the completion of the Tamiami Trail through the Everglades in 1928. The county bears his name. After the war, the resort logic compounded: Port Royal, platted by advertising executive John Glen Sample on the city's southern tip, became one of the wealthiest neighborhoods in America, and the golf courses multiplied until greater Naples held one of the densest concentrations in the country. The wealth stayed and organized itself: the philanthropy that sustains Artis, Naples, the Baker Museum, and the steady expansion of NCH Healthcare System is the modern expression of the original promise.

The pier tells the whole story, including the honest part. It has been wrecked and rebuilt across six storms and 138 years, most recently destroyed by Hurricane Ian in 2022. Its sixth rebuild broke ground in January 2026, engineered higher and stronger, with reopening expected in 2027. That is Naples in one structure: a town built deliberately as a paradise, wealthy enough to keep rebuilding it, on a coastline that periodically collects the premium.