Until the 1950s, Old Naples, Florida thrived as a little oasis along the Gulf of Mexico known to select vacationers and glamorous celebrities who had discovered its charms in the 1920s and 1930s.

In the late 19th century, General John S. Williams, a senator from Kentucky, recruited Walter Haldeman, the wealthy publisher of the Louisville Courier-Journal. In 1885, the two sailed up the southwestern coast of Florida after reading detailed survey reports from various expeditions along the coast. Mesmerized by the dazzling beach and natural bay to the east, the two quickly moved in to maximize the area’s potential. By 1889, they had built a 16-room hotel and built houses on the beach. Haldeman eventually purchased Williams and became the owner of the town, including 8,600 acres of land. In 1912, another developer purchased the Haldeman property, paving the way for a new chapter in Naples history. The completion of the Tamiami Trail in 1928 linked Tampa, Naples, and Miami, allowing additional generations to discover the beauty of Old Naples.

In the early 1930s, winter visitors began to frequent the area, despite the dearth of a downtown area. Gary Cooper, Gertrude Lawrence, and Gloria Swanson were rumored to hold court at the popular 41 Club (named for the lonely highway, US 41, that ran through Naples at the time). Charles Lindbergh and his wife, Ann, flew in to pick up supplies on their way to retirement on Sanibel. Downtown businesses included a garage, train station, liquor store, and gas station, all located at the intersection known as Four Corners. Although the train depot discontinued service in the 1970s, the Depot remains a historic landmark and a place for community gatherings and events.

The history of Naples would not be complete without the mention of two other colorful figures: Mamie Tooke and Cory Osceola. Mamie Tooke, the “Mother of Naples,” opened the first bank in Naples in 1949 and taught local residents financial skills, such as saving and managing their money. Many of these early depositors eventually became some of the largest landowners in the area. Cory Osceola was the reigning member of a well-established Seminole Indian family whose descendants helped build the “Chickees” or cypress pole buildings with saw palmetto roofs. Today, these distinctive structures add to the character of Florida’s southwest coast.

The ancient history of Naples is marked by a unique cast of characters who helped shape the beauty and distinctive character of the community. The area now extends from South Gulf Drive to the section around the Naples Pier all the way south to Aqualane Shores.