The Winter Retreat History of Naples FL

Every fall and winter, residents of our northern US states pack their bags and head down to Florida, where the weather is warm, the snow is non-existent, and the beaches spread for miles and miles.  It’s hard to believe that Naples FL was once considered too hot, humid, and swampy to ever consider visiting, let alone taking up residency, but a lot has changed from our city’s humble beginnings - specifically, air conditioning and other useful technology - and Naples is now one of the most popular destinations for those considering a winter retreat from their snowy homeland.  Let’s start from the beginning.  

Thou Shall Not Pass

Those resourceful enough to endure Florida thousands of years ago were the early Native Americans, who used the waterways to quench their thirst and hunt for game.  The Calusa knew how to make their away around our difficult lands of swamp, wildlife, and heat, and survived for thousands of years living off the land that others were denied by the natural landscape that obstructed their path and their unwillingness to risk their lives trying to overcome it.

The Spanish came to claim the land in the 1500’s, thereby forcing the Calusa from their home and settling in the areas that were somewhat inhabitable.  Trails that had been forged by the Calusa and used to hunt game and move along the Caloosahatchee River - such as State Road 82 (The Immokalee Trail) - were taken and used for settlements.

For close to 300 years, Spain kept control over Florida until it become a US territory in 1821.  Too much heat and humidity for city folk, Florida became a residence for cattlemen, ranchers, farmers, fishermen, who started to create a community within Southwest Florida, including what would later become Naples FL.

Naples FL Takes Shape

Enduring the heat, humidity, and lackluster land conditions, the early US settlers began to create a community, building small “businesses” and learning the lay of the land. One such business was Ted Smallwood’s Store on the Chokoloskee Bay, which became the trading post to go for them, and the Seminole, to sell their game for flour, sugar, rice, and any other essentials they could not find in the wild.  It is now a museum that educates travelers on the early days of Southwest Florida.

In the late 1880’s, the Naples Town Improvement Company was founded by a group of Tallahassee businessmen, who were selling lots for $10 to increase the number of visitors to the area.  In 1887, one year after establishing the company, it was taken over by Civil War general and U.S. Senator, John S. Williams, and his group of prominent Kentucky businessmen, and fellow Kentucky native and American newspaper publisher, owner, and businessman Walter N. Haldeman, who purchased 3,712 acres between the Gulf of Mexico and Naples Bay (to be named later) for $11,136, or $3 per acre. The Naples Company had successfully discovered an area that could be inhabited and could create the perfect place for winter visitors, much like Sarasota FL to the north.

Although The Naples Company was able to build a 600-ft pier, a general store, a post office, and a hotel, there were only about 80 people that used Naples as a winter retreat, thanks to the difficult passage through the rough and swampy terrains.  The Naples Company could not survive with such little return on their investment and the company fell apart due to the financial burdens of their gamble.  Walter N. Haldeman, who still saw potential in the area, purchased the company at auction in January 10, 1890.  This auction was held in the area’s first hotel - The Naples Hotel - located two blocks from the 600-ft pier on a small piece of land between the beach and the Naples Bay.  He purchased the company for a whopping $50,000, ­including 8,600 acres of land, the Naples Hotel, the 600-ft pier, the Fearless steamship that was used to transport guests to and from Naples and General Williams' house. 

Continued Growth

For 30 years, Naples FL remained largely the same, surviving on the few winter visitors that were brought in.  Then, Ed Crayton, a successful land developer from St. Petersburg, visited Naples and purchased all of the Haldeman’s property - minus his residence - in the early 1900s.  He married Haldeman’s son’s secretary and settled in Naples to further develop the land.  Together, Ed and Lindsey Crayton made several changes to Naples, including bringing electricity to the town in 1926, the Seaboard Air Line Railway in 1927, and the completion of the Tamiami Trail (more on that later).  Ed Crayton died in 1938, but his wife inherited the estate and held onto it until the 1950s.

While Haldeman and Lindsey Crayton developed Naples, Barron Collier, a self-made advertising millionaire, also made several investments in Naples FL in the early 1900s. At that time, there wasn’t a connecting road from the east coast of Florida to the southwest coast and the state of Florida didn’t have the funds to cover the construction.  Barron Collier stepped in to finance the project and, in 1923, construction began on Tamiami Trail.  As a thank you for his willingness to fund the road, the state of Florida carved out Collier County from the south end of Lee County.  Tamiami Trail would take 13 years, $8 million dollars, and some help from Ed and Lindsey Crayton to build, but it opened Naples FL and the rest of Southwest Florida to the many people that would later discover our paradise coast.  Barron Collier also bright paved roads, telegraphs, and new businesses to the area.

The First Naples Boom

World War II brought the first real boom in population to Naples FL, thanks to the creation of the U.S. Army Field (to be given back to Naples in 1947 and called the Naples America Airport and then the Naples Municipal Airport in current time) for flight training.  Hundreds of men were assigned to the base and, after the war, many of those veterans returned to Naples to purchase houses, build businesses, and make Naples FL their home.  

Discover the beauty and history of Naples FL when you plan your visit to our paradise.  You may find your own winter retreat among the gorgeous luxury home communities throughout the area, including Mediterra Naples, an 11-time winner for Community of the Year.