A Look Inside the Rich History of Naples, Florida

David R. Bartley, Sr
Published on March 16, 2020

A Look Inside the Rich History of Naples, Florida

Naples, Florida is called Paradise Coast for good reason. Naples and its surrounding area are perfect destinations, not just for a great Florida vacation but it’s also a coastal paradise you can call home.

While most people know this place as a wonderful vacation destination, Naples is steeped in history dating back to the Calusa Indians, who first made contact with Spanish conquistadors during the 1500’s. Calusa Indians were the first to call Naples their home and they inhabited most of Southwest Florida. During the peak of the tribe, as many as fifty thousand members established settlement throughout the region.

During the late 1800s, while the United States was performing surveys of Southwest Florida, then senator, General John S. Williams from Louisville heard of the lovely descriptions of the area and decided to visit to buy land and develop a community. For this expedition, he recruited Walter Haldeman, who owned the Louisville Courier Journal newspaper in 1885. As the group sailed past the present location of what is now known as Naples, they spotted a beach line that stretched for miles. When they spotted a lovely bay just behind the white sandy beach, they knew they had found paradise.

Naples Town Improvement Company

In 1886, the Naples Town Improvement Company was founded to establish a town named Naples, similar to that of the Italian peninsula with the purpose of developing it as a winter retreat. The company bought more than 3,712 acres between the Gulf of Mexico and what is now known as Naples Bay for just $3 per acre.

First Beach Homes and Hotel

Within the next few years, Haldeman and Williams built their first homes on the beach and hired a firm from Fort Myers to build a pier while survey teams did the planning to develop their dream city. Right at the center of the town was a 16-room hotel located two blocks inland from the pier. When the hotel first opened in 1889, Rose Cleveland who is the sister of President Cleveland, was the hotel’s first celebrity guest. Haldeman and Williams were able to build a 600-foot pier reaching into the Gulf of Mexico, a post office, a general store, and a hotel. Even today, the Naples Pier remains an iconic symbol of the city.

By the summer of 1888, the city of Naples only had a population of around eighty people. Despite their bright ideas, Haldeman and Williams incurred increasing debts due to slow land sales. Haldeman eventually bought the sole ownership of the Naples Company during an auction in 1890.  Haldeman’s purchase included the Naples Pier, the Naples Hotel, a steamship and more than 8,600 acres of land. Until his death, Haldeman continued to advocate for Naples but the planned development for the city was on hold. Despite these setbacks, Naples continued to be a quiet winter retreat for wealthy families from Kentucky and Ohio until the arrival of Ed Crayton.

A wealthy developer from St. Petersburg, Ed Crayton set his sights on Naples in the 1900s. When he married the secretary of Haldeman’s son, Crayton bought all of Haldeman’s land and property.  Ed Crayton was credited for all the modern development in Naples until his death in 1938.

During the 1920s, railroads and highways were built, which lead the way to the City on the Gulf. This major development has paved the way for modern Naples and lead to even more development. Electric power services were initiated in 1926 and rail service was introduced in 1927. In 1928, the renowned Tamiami Trail that connected Tampa to Miami passing through Naples was completed.

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