Chapter 24


(Notes by Gayle Pence and Nanette Laurion)

1884-1894 – The Early Years and Homesteading

In 1880, Sanibel Island was opened to homesteading. There were few requirements, and if one could withstand the sweltering heat, relentless mosquitoes, lack of most creature comforts, and almost total isolation, it was just about bearable. Quite simply, to be given 160 acres of land, one would have to be at least 21 years old, be able to work the land for five years, and have never borne arms against the United States Government. Since most of the island men had gone to war, a large number of the homesteads were registered under the names of women. The Woodrings were the first homesteaders. The population grew to 120, and the Barnes family built the first hotel and called it “The Sisters.”


Anna Woodring and her family homesteaded on Sanibel in 1895. At the age of 44, after 25 years of marriage, she was widowed. At that time, she became the sole provider for her five children. She established a boarding house in the family home and called it “The Woodring House.” It catered to fishermen, tourists, and “drummers.” The Woodring House was Sanibel’s first lodging establishment.


Jean Barnes and her husband built and Jean operated “The Sister’s Hotel” (today’s Casa Ybel). It was greatly through her efforts that the first church was erected on hotel property. Jean was married to the Reverend Barnes. They moved here from Kentucky, encouraging many others to follow.


Jennie Doane, as postmistress of Wulfert, shipped out more than 1,000 crates of fruits and vegetables a week. As an advocate for women’s suffrage, she was both opinionated and strong willed. One of her opinions was that a woman had the right to dress according to the job she held. Jennie wore pants under her skirt, which was considered rather “fashion forward” for the time. Uninvited guests reported being served “six walnuts rolling around on a plate.”


Jane was a single-minded woman who saw life on this rather remote island as both an adventure and an opportunity. She homesteaded 160 acres. Jane erected two piers: Mathew’s Wharf, a commercial pier on the bay that made it possible for the ferry to dock and supplies to be delivered, and a pleasure pier on her own gulf-front property that featured both a bathhouse and a pavilion. Jane lived next door to Hallie Matthews. Although they shared the same last name, they were not related. Jane paid to take her meals at Hallie’s. Others followed and Hallie found herself in the home restaurant business. When Jane died, Hallie inherited Jane’s house through a trade with Jane’s niece, and The Matthews hotel was established.

1895-1910 – Great Expectations

Sanibel’s reputation as a farming community continued and Sanibel tomatoes, considered to be just about the best, were served in upscale restaurants across the country. Land was plentiful and in 1896, with the population at 350, the first Sanibel School was built. The Spanish American War raged and in 1899, Frank Bailey founded the Sanibel Packing Company.


Hallie was a Sanibel homesteader who built three houses directly on the beach. Folks arriving to enjoy the island “flavor” would be allowed to stay in one of the cottages as long as they agreed to take their meals with Hallie. Hallie, a rather “no nonsense” lady, was admired for her determination and business savvy. She is credited with establishing The Matthews hotel, which later became The Island Inn. Hallie was grandmother to Francis, John, and Sam Bailey.


Laetitia and her daughters were the island’s first teachers and full-time residents. They founded and ran the private Sanibel Home School. Laetitia’s Homesteading Certificate, in her name alone, is dated 1895 and signed by President Grover Cleveland. Laetitia ran a boarding house in her home, The Gables. She was also the island’s first postmistress. Laetitia was regarded as strong, positive, and resourceful. It was the Nutt family who donated the land for the Community House.

1911-1928 – SUN AND STORMS

The Kinzie Brothers started the ferry service to Sanibel in 1926. A year later, Charlotta Matthews opened her tea room at the ferry landing, and the first Shell Fair was held.


Annie Meade Matthews, a schoolteacher, was the wife of Frank Bailey and mother to Francis, John, and Sam Bailey. Annie was actively involved in the Community Association and was a devoted member of the Community Church. She died young, and her sons remember her with great affection and pride.


Affectionately dubbed “Chebum” by her nephews, Francis, John, and Sam, she established and ran Miss Charlotta’s Tea Room at the ferry landing. Charlotta wore numerous hats throughout her days in Florida, including that of manager of the day-to-day operation of The Matthews, which later became the Island Inn. By her family, she is most remembered for her devotion to all of them before and after the untimely death of her sister, Annie Meade Bailey.

1929-1954 – Depression and War

Remarkable changes occurred on this tiny barrier island. In 1939, the population had decreased to just 100. Electric service came to Sanibel in 1942 and was followed by the founding of the J.N. “Ding” Darling National Wildlife Refuge in 1945. The island was heavily impacted by the 1949 hurricane that brought 163 mph winds. Once again, our island sisters firmly planted their hats on their heads and persevered.


Alice O’Brien (born in 1891) was from St. Paul. Her family was in the lumber business and she would arrive on Captiva aboard her yacht “The Wanigan,” so named for a trunk used in lumber camps to store anything that just might be wanted again. According to her family, Alice was an astute businesswoman, adventurer, sailor, philanthropist, fisherwoman, and animal lover. She supported the early organization of the Sanibel and Captiva Island Association. She was a dear friend of “Ding” Darling and his wife and shared their concerns regarding the negative impact of beach erosion and red tide on our islands. In the early 1960s, she provided the much-needed seed money for the Sanibel-Captiva Conservation Foundation. In WWI, she was a mechanic and Red Cross ambulance driver. Alice died in 1962 while on her way to visit the Darlings.


Esperanza was the wife of Sam Woodring, Jr. and came to Woodring Point in 1917 at the age of 16. She remained in the same house until her death in 1992. Her husband’s death in 1942 left her with five-year-old Ralph to rear on her own. She continued to fish commercially and became one of the island’s most sought-after fishing guides. An avid reader, she was self-educated and had a love of the area and its natural environment. Esperanza was determined and resourceful. Her hard work allowed her to retain the Woodring homestead on the bay and to purchase additional property on Periwinkle Way where the Bait Box is located today.

1946-1959 – Growing Again

For nearly 20 years, Sanibel was somewhat forgotten. After the war, people with leisure time and money to spend discovered its fishing, shelling, and sandy beaches. Small family-owned motels sprang up. The Kinzie ferries were back on schedule, telephone lines were strung, and Sanibel made an attempt to shed its unofficial title as “Mosquito Capital of the World.”


Mary Bell was the original owner of the Seahorse Shop and Cottages. Many recall that it had the most unusual little outdoor market atmosphere with a row of doors that opened back, leaving the entire front adrift with the sounds and winds of the sea. It provided an outlet for the shell jewelry made by her husband. Today the Seahorse Shop is the second-oldest retail shop on the island. Mary’s involvement in numerous pre-city issues aided in the incorporation of Sanibel.


Priscilla Murphy established the island’s first real estate company. At the time, Lee County was forever changing the name of Sanibel’s main thoroughfare. Priscilla found the names inappropriate for this island paradise and rather forcefully suggested to the county that the name be changed to Periwinkle Way in celebration of the vibrant flowers that grew wild along its roadside.


Mozella Jordan was a crusader for equality in education for all island children. Along with Mary Bell, she was instrumental in the Sanibel School becoming the first integrated campus in Lee County. Mozella and her husband were the first African American couple to purchase property on the island. Mozella was dedicated to her family and church. She became Sanibel’s most popular caterer.


Dorothy Stearns was a remarkable wife, mother, and grandmother. She was an avid boater and could captain a craft with the best of them. Dorothy was a dedicated sheller and shell crafter, publishing books on the subjects. Her family remembers that her home was filled with shell crafts. She was an accomplished, self-taught artist and the inspiration for the naming of Gramma Dot’s restaurant. She baked the pies and cakes for the restaurant. Dot was involved in the organization of the Shell Fair and had her own booth. Dorothy often used tarpon scales to decorate mirrors. This fun-loving woman enjoyed going out dancing, exercised daily, and was a phenomenal marksman and avid fisherman. Her family shares a smile in remembering a time when, at over 90 years old, she asked, “Do you think that I could pass for 80?”

The 1960s and forward – Island Life Changes Forever

Much to the dismay of most islanders, 1963 saw the opening of a causeway that linked the island to the mainland. Soon after this, Lee County revealed its plans for Sanibel. This plan included high-rises, increased commercialism, and a population of about 90,000. In 1974, the residents of Sanibel decided to take control of their own destiny, designed a mission statement, and voted to incorporate. The city of Sanibel was born.


In 1974, Zee Butler chaired “Sanibel Tomorrow,” an organization that was dedicated to incorporation. She became the first female mayor and served in both 1974 and 1978. Zee is remembered for her exceptional approach to problem solving and her great stamina. She was ever watchful over city government. In his eulogy Porter Goss remembered her for saving the beaches from “man’s improvements,” protecting the wetlands, and her tireless involvement in the creation of Sanibel’s bike paths.


Elinore Dormer moved to Sanibel in 1924. She was a noted island historian and is credited with coining the phrase “Old Town Sanibel” in reference to the area around the Seahorse Shop on the island’s east end. As a member of the Historical Committee, she contributed to the drafting of the city’s comprehensive land use plan. Elinore was instrumental in petitioning the federal government for de-segregation in 1964 and was involved in the founding of the Sanibel Historical Museum and Village. She is the author of “The Seashell Islands,” considered to be the most definitive history of the islands.


Emmy Lu Lewis was known as “the great lady of island conservation.” She and her husband began wintering on the island in 1942. She was instrumental in the establishment of St. Michael and All Angels Episcopal Church and was an active member of the “Ding” Darling Committee (which later became the Sanibel-Captiva Conservation Foundation). Emmy Lu was its first chairperson.

We offer thanks to the many island women who embraced this almost forgotten little barrier island and battled through hardships and nearly unbearable circumstances just to call it home.
Here’s to the years when rare shells rolled in endlessly, water was collected in cisterns, mosquitoes embedded themselves in window screens, Periwinkle Way was a dirt road, and the people of Sanibel had the foresight to preserve and protect its unique environment.