Once, the only people to stroll Naples’ seven miles of white, sandy beaches, were the Caloosa Indians. The first settlers, Roger Gordon and Joe Wiggins, arrived in Naples in the late 1860’s. A river and two inlets still bear their names.

Throughout the 1870’s and ’80’s, magazine and newspaper stories telling of the area’s mild climate and abundant fish and game likened it to the sunny Italian peninsula. The name of Naples caught on when promoters described the bay as “surpassing the bay in Naples, Italy.”

In 1887, a group of wealthy Kentuckians, led by Walter N. Haldeman, owner of the Louisville Courier-Journal, purchased virtually the entire town of Naples. One of the first improvements Haldeman and The Naples Company made was to build a pier 600 feet into the Gulf of Mexico. The unusual “T” shape allowed large ships to dock easily. Despite being destroyed and rebuilt three times, the pier’s “T’” shape remains.

Naples quickly gained a reputation as a winter resort. Social life revolved around the Naples Hotel, which played host to celebrities such as Rose Cleveland, Thomas Edison, Harvey Firestone, Greta Garbo, Hedy Lamarr, and Gary Cooper. As the town of Naples went up, so did the price of property. The cost of a beachfront lot soon reached $125.

In 1911, Barron G. Collier, who had made his fortune in streetcar advertising, visited nearby Useppa Island. He was so taken with the area that he bought over a million acres of untouched swampland - including most of Naples. Collier believed that Florida’s west coast could enjoy the same boom that the east coast was experiencing in the 1920’s; but first it was necessary to bring in road and railroads.

Based on Collier’s promise to help build the Tamiami Trail, in 1923 the state legislature created Collier County, of which Naples is the county seat. Collier spent more than $1 million of his own money to construct the Tamiami Trail, which opened in 1926 as the only paved highway linking the state’s two largest cities—Tampa and Miami. Collier died before he could see his dream come true, but come true it did. Today, Naples enjoys unparalleled prosperity. And the area’s unrivaled sport fishing, hunting, boating, sun bathing, and beach combing attracts people today just as it did a century ago.

*Courtesy of Dining and Doing Guide