Roger Gordon and Joe Wiggins were among the first settlers who arrived in Naples in the late 1860’s. A river and two inlets still bear their names. Soon after settling, stories spread of the area’s ideal climate and fishing likened it to the sunny Italian peninsula. Developers described the area as “surpassing the bay in Naples, Italy” and the name Naples stuck. In 1887 the Naples pier was built 600 feet into the Gulf of Mexico. The landmark pier has been destroyed and rebuilt a few times since, the original shape remains.

Naples quickly gained popularity as a winter getaway. Thomas Edison, Harvey Firestone, and Henry Ford were a few of the early figures that frequented the area. In 1911 successful streetcar advertiser Barron Collier visited Useppa Island and purchased over a million acres of untouched swampland mostly in Naples. Collier promised to help develop the area, and in 1923 the state of Florida created Collier County, of which Naples is the county seat. Barron spent more than $1 million to build the Tamiami Trail, which opened in 1926 to link the state’s two largest cities Miami and Tampa.