Women’s History Month is a great time to offer thanks to the many island women who embraced this almost forgotten little barrier island and battled through hardships and near 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 – often under the guidance or following the example of their women – had the foresight to preserve and protect its unique environment.

1884-1894:  The Early Years and Homesteading


Jane was a single-minded gal who saw life on this rather remote island as both an adventure and an opportunity. She homesteaded 160 acres. Jane erected two piers: Matthew’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, later the Island Inn, was established.

1895-1910: Great Expectations


Hallie Matthews 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 John, Francis and Sam Bailey.

1911-1928:  Sun and Storms

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


Anne Mead Matthews, a school teacher, was the wife of Frank Bailey and mother to Francis, John and Sam Bailey. Anne was actively involved in the Community Association and a devoted member of the Community Church. Her sons remember her with great affection and pride.


Affectionately dubbed “Chebum” by her nephews, John, Francis and Sam Bailey, she established and ran Miss Charlotta’s 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, both before and after the untimely death of her sister, Anne Mead Bailey.