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Although the story of Anne Bonny and Calico Jack honeymooning on Estero Island may be less fact than fiction, it is a refreshing part of the history of Estero Island. According to Jack Beater’s book, Pirates and Buried Treasure on Florida Islands, Anne Bonny was the daughter of a wealthy lawyer who lived in North Carolina.

For many years, Estero Island was home to Calusa Indians, Cuban Fishermen, Spanish Missionaries, and some say, pirates. It was not until the mid-1870s that the first family settled on Fort Myers Beach. Sam Ellis, his wife, and his son, George Underhill, settled at the end of Connecticut Street where the Mound House now sits. Although Ellis and his family ended up moving to Sanibel where they homesteaded a track of land near Tarpon Bay, George’s son (also named George) returned to Fort Myers Beach where he raised his family.  The Homestead At of 1862 brought new settlers to the island. Intrigued by the idea of getting free land, the settlers came from all over the United States and Europe hoping to prove their claim by living on the land for five years, clearing it, farming it, and improving it.

Opened in 1912, the Winkler Hotel was the first hotel on the island. The early part of the 20 th century brought more development as the first subdivisions were platted on Fort Myers Beach. H.C. Case platted the first of these subdivisions in 1911. Originally this was part of the Robert Gilbert homestead. Starting at Connecticut Street, the subdivision extended about three quarters of a mile both north and south. At this time, Estero Boulevard was called Eucalyptus Avenue. This was a north-south shell road that ended at Connecticut. If you wanted to travel farther south, you would need to continue your journey on the beach. Another five years passed before T.P. Hill subdivided a large tract started at Crescent Street and ending just south of Gulf Drive. The lots that were on the beach side of Estero were normal sized lots. However, the lots on the other side of the road were approximately 9-10 acres running from the street to the bay. Land on the island in the 1900s was filled with brush and palmettos that were so thick no engineer would agree to complete an accurate survey because wading through the mangroves to accurately measure an acre of “cheap land” did not seem like a good idea. Three years later, Seagrape Subdivision was put on the market. These lots were located on Mango and Avocado streets in 1919 (Avocado Street was renamed Chapel Street in 1952). At this time, Crescent Beach (as it was called at that time) was becoming a popular destination for people living in town. In 1912 the Winkler Hotel was opened at the end of Pompano Street. At this time, the island was only accessible by boat. The guests would arrive by schooner and would dock at a pier on the gulf side in front of the hotel.

Yesterday I was surfing the Internet, and I came across an article about haunted restaurants. This article mentioned the Whale (formerly the Beached Whale and before that the Mermaid Club) as being haunted by the ghosts of Jim and Mary Galloway (I covered their murder in an earlier posting). Suddenly, I remembered reading about another haunted restaurant on the island: the Holmes House. This led me down a rabbit hole as I got caught up in trying to learn more about the ghost that was supposed to be the daughter of the restaurant owner who had died (I can’t remember how she was supposed to have died). Unfortunately, I came up empty on the ghost story, but I did learn some interesting facts about this lost icon of Fort Myers Beach.

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