From pioneering settlers to visionaries like Harry Higel, John Ringling and Bertha Palmer, the island’s past laid the foundation for its rise as a vacation destination
By Ned Steele
Romance, ambition and even a murder mystery are part of Siesta Key’s past. But history is driven by people. Here’s a look at some figures from long ago who helped make the island what it is today.
This article draws heavily on An Illustrated History of Siesta Key by Philip M. Farrell and Thomas Philip Farrell, a father-son team, and an interview with Philip Farrell. The book is available on Amazon.
As Farrell told the Siesta Sand, mainland Sarasota had to develop first before Siesta Key could emerge as a destination. The two histories, he said, are “synergistic and interdependent.”
The story begins with the Calusa Indians and the Spanish, but Sarasota’s modern history starts in 1842. A young Georgian, William H. Whitaker, saw opportunity in the Gulf waters and took advantage of a federal land grant program to become the area’s first white settler. An entrepreneurial fisherman, he harvested huge numbers of mullets that swarmed the waters to escape sharks. Whitaker sold the catch to Cuban Catholic traders, especially during Lent.
Shifting to land-based enterprise, Whitaker became a successful cattleman by rounding up native cattle roaming the fields and started the area’s first orange groves, leaving a legacy that extended to his descendants.
The fishing industry also attracted Captain Lewis Roberts, of Roberts Point Road fame, to the area in the 1870s. He married Ocean Deep Hansen, and the couple homesteaded across the bay on Roberts Point. Today, visitors may notice Ocean Boulevard on the Gulf — named for Ocean Deep Hansen Roberts.
Captain and Mrs. Roberts are considered the founders of Siesta Key’s hospitality industry. They started a boarding house and restaurant for locals, famous for clam chowder made from clams the family dug themselves. With growing popularity, the boarding house expanded into the Roberts Hotel to accommodate northern visitors.
Soon, Captain Roberts partnered with Siesta Key’s most legendary figure: Harry Higel. A visionary real estate developer who later became Sarasota’s mayor, Higel worked with Roberts on projects that transformed the sparsely populated island. With a third partner, they platted a major residential and commercial subdivision called Siesta on the Gulf. Until then, the island had been known as Clam Island, Little Sarasota Key, Muscle Island and Palm Island. Higel is credited with naming the island Siesta Key, intending it as a relaxing getaway apart from Sarasota. The Roberts Hotel became the Siesta Hotel.
Under Higel, streets were laid, canals dredged, and lots developed. He promoted the island extensively, but accessibility was limited. Recognizing the coming automobile era, he pushed for a bridge and roadways to bring northern visitors to the island. Higel built a two-story luxury hotel, the Higelhurst, which opened in 1915 with a lavish party. A month later, the hotel burned. Plans to rebuild never materialized.
Tragedy struck in 1921 when Higel was found beaten to death on Beach Road. Rube Allyn, a former Sarasota Sun editor, was arrested on circumstantial evidence but was acquitted after 61 days. The case remains unsolved. Despite his violent end, Higel set in motion forces that made Siesta Key a destination. “He is arguably the most important person in the development of Sarasota and Siesta Key,” Farrell said.
Two wealthy outsiders also shaped the island’s growth. Bertha Palmer, a Chicago socialite, bought more than 80,000 acres around Sarasota in 1910, developing land and attracting other northern investors. She built a home on Siesta Key in 1918, restored in 2020. Palmer is also credited with inventing the brownie.
John Ringling first visited Sarasota in 1909, investing in real estate with Owen Burns. They created vacation destinations offshore, including St. Armands, Lido and Bird Keys, and built the first bridge to reach them. Ringling’s famous home, Cà d’Zan, was begun in 1924. In 1927, he made Sarasota the winter home of his circus, bringing attention and visitors to the area — many of whom gravitated to Siesta Key. Ringling also persuaded the New York Giants baseball team to hold spring training in Sarasota, further connecting the island to recreation and tourism.
Siesta Key also attracted notable visitors like Thomas Edison, who visited the Out-of-Door School (now Academy) near Fort Myers, and First Lady Eleanor Roosevelt, who visited relatives on the island. Their presence helped enhance the island’s status as a premier getaway.
Modern development has transformed Siesta Key, but its early settlers, visionaries and even tragic figures laid the foundation for the island we know today.
