The Caloosa Indians inhabited the wild lands of Southwest Florida for thousands of years. Before them were gatherers and hunters who migrated south after the last Ice Age. During the 1700s, Creek Indians from Georgia and Alabama joined with escaped black slaves, creating a new group of Indians called the Seminole. The first known settlers in Naples were Roger Gordon and Joe Wiggins who arrived in the 1860's. Newspaper articles praised the area for its mild climate and likened it to Naples in Italy—hence the city’s name. The area was ripe for citrus, agricultural and cattle industries. Tourism quickly followed.

In 1887, Walter N. Haldeman, owner of the Louisville Courier-Journal, purchased the entire town of Naples and built a 600-foot pier into the Gulf of Mexico. Although it was destroyed several times, the pier has always been replaced and it remains a landmark today. It became a winter resort for celebrities and wealthy northerners after the construction of The Naples Hotel. In 1911, Barron G. Collier bought one million acres of swampland, believing the area could be developed just like Florida’s east coast. He built the Tamiami Trail in 1926, the only paved road between Miami and Naples. The county is named after him. The 1920s land boom in Florida saw fast-paced economic development, but the 1929 Depression brought it to a halt. The end of WWII saw a revival of community development and it has continued to this day with luxury resorts, , culture, and nature’s wonders.