As a visitor to Historic Key West you have many ways to immerse yourself in our history.

A look into the ‘recent’ past of Key West, circa 1965, can be found on this page called ‘The Way We Were – Key West’. This collection of photos taken by the property appraisers office was lovingly put together by our resident volunteer historian, Linda Todhunter, who works with us at our Merlin Guesthouse. She definitely has some good stories to tell!

We also recommend that you use one of our three favorite historical guides to explore our rich past.The first is by our friend Teresa Willis who has put together  Sharon Wells’ Key West Walking Guide App  The Guide offers seven incredible self-guided tours with information on Key West’s architectural, history, its culture, literary and artistic heritage. It ranks high on our list because each building or marker is accompanied by beautiful past and present photographs, making this an engaging walk through time.

Our friends at the Key West Historic Markers Project have created a fascinating free tour that leads you around the island using a system of markers that identify 7 categories of historic sites and buildings, with an explanation that can be seen there or accessed by your phone.

A third option for touring the historic sites of the island is the Pelican Path Self-Guided Tour of Key West. You can print the tour and take it with you as you meander from one location to another, learning more about the beautiful homes and other sites you see on your journey. We like to rent bicycles for our tours on the island, stopping at some cafe’s for drinks and lunch along the way.

We are very excited that 2012 marks the Centennial Celebration of Henry Morrison Flagler’s Florida Keys Over-Sea Railroad which connected Key West to the existing Florida East Coast Railway.

The first journey to Key West left New York City on January 20th, 1912.  A special Pullman sleeping car train with three bedrooms, a kitchen, salon and private bath housed Flagler, who was 82, and his wife Mary Lily Kenan. Their historic ride ended in Key West as the train arrived at 10:30 a.m. on Jan. 22nd. Come join us as we celebrate his achievements at events throughout the year.

According to the historian Jerry Wilkson,” Key West, like the other Florida Keys, began as a coral forest under the sea water where marine life was its population. As the polar ice caps reformed and the sea level dropped, terrestrial plant and animal life found its way. Soil was formed by decaying organic matter and storm actions. For millenniums the ocean continued to drop and the ocean currents, wind currents, birds, etc. continued to propagate the islands. Eventually human life forms found their way. This pyramiding of trillions of life cells, along with the forces of nature, produced an island called Cayo Hueso by early Spanish travelers.

The Spanish normally used “isla” for island and “islet” for small island. At least in the New World, they appear to use “cayo” and “cayuelo” for a very small island. The English used “Cay” or “Kay” such as Cay Sal Banks. Cay is pronounced by Americans as the letter “K,” but by Englishmen as the word ‘Key.’ I am not certain if the written and the pronounced versions made any difference. Anyway, English maps of the Keys made just prior to the Revolutionary War of 1776 used the word “Key.” A Colonial American court record of the “Libel of Dennis and Allen vs the snow St. Fermin alias Britanis” in 1744 used the word “Keys” referring to the Florida Keys. This is one case where an American court reporter might write ”Key’ when an Englishmen prounced ‘Cay.’

John W. Simonton purchased the island on January 19, 1822 from Juan Pablo Salas, who had acquired it as a Spanish Land Grant in 1815 from Don Juan de Estrata, but as a U.S. Territory the original Don Juan de Estrata Land Grant to Salas had to the confirmed – no U.S. deed could be granted.  In reality it went round and round with claims and counter claims. Attempts to follow these look like a spider web. John Simonton soon took on three northern partners: John Whitehead, John Fleming and Pardon Greene. On the scene arrived General John Geddes of Charleston who had also purchased Key West. It was discovered that Don Juan Salas had sold it twice, first to John Strong, a lawyer no less, and then to Simonton. As if this were not bad enough, Strong had also previously sold Key West to George Murray before John Geddes. In summary, Salas sold it twice, Strong and Simonton, and Strong twice, Murray and Geddes. Simonton had already divided it up amongst three others: Whitehead, Fleming and Greene. Greene made several strategic moves by buying up claims in his name. On May 23, 1828, Congress acknowledged the land grant of Salas was confirmed. Simonton as the legal owner. We might surmise that this was Florida’s first land scam. Amazing as it legally appears, the Territory of Florida with an Act of Incorporation incorporated the City of Key West on January 8, 1828. I have never fully researched this, but my understanding with Monroe County’s Territorial Representative Richard Fitzpatrick changed its name to the Town of Key West on November 28, 1828. Fitzpatrick was the one who made Indian Key the County Seat of Dade County.”


This red brick home was built by Captain Martin Hellings in 1892. Captain Hellings was the manager of the International Ocean Telegraph Company. The importance of his job is obvious if you consider that before the advent of radio and telephones, the telegraph was the only way to communicate long distances.

The Captain’s wife, Eleanor, was the daughter of William Curry, who was one of the foremost merchants of his time and is believed to be Florida’s first millionaire.

Eleanor Hellings was the founder of the Key West branch of the Christian Science Church.

In 1940, the building was purchased by the Key West Woman’s Club. During the first 20 years of their ownership, the house had two main functions. The left side of the building was maintained as the only public library in Monroe County and the rooms on the right side were club rooms. The Women’s Club was instrumental in the building of the Monroe County Library in 1959 located at 700 Fleming Street in the Historic District.

Behind the house, the red frame structure with a gabled metal roof was once a carriage house for a horse used by the U.S. Post Office. It is currently the home of the Red Barn Theatre.