The Florida Channel comes to Indian Key

An aerial shot of Indian Key taken in 1980 shows the town square.
An aerial shot of Indian Key taken in 1980 shows the town square.

Indian Key might be the most interesting island in the whole of the Florida Keys, historically speaking. Unlike the spectacle that is Key West, it does not look like much while driving past on the newly anointed Indian Key Irving R. Eyster Bridge. 

Once upon a time, however, the seemingly nondescript island was home to the second largest community in the whole of the Florida Keys archipelago and today represents the chain’s only bona fide ghost town. The designation seems a fitting end for an island once called <i>Cayouelo de Matanzas<i> or, roughly translated, Little Slaughter Island.

One of the first times the place name Cayouelo de Matanzas appeared on a map was a 1733 chart showing a Spanish salvage operation that likely included the sinking of the San Pedro, a casualty of the hurricane that devastated the 1733 Spanish Treasure Fleet. 

Writer and mapmaker Bernard Romans wrote of the island in a work published in 1775, “This key is called Matanca i.e. Murder from the catastrophe of a French crew said to have amounted to near three hundred men, who were unfortunate enough to fall into the hands of the Coloosas, which savages destroyed them to a man on this spot.” 

While the story is colorful, there is no proof the event actually occurred. 

When George Gauld published his chart in 1775, he identified the island as both Matanzas and Indian Key. He also noted that the Bahamians identified the island with the names Indian Key and Kay Comfort. 

F.H. Gerdes wrote in his guide Reconnaissance of the Florida Reef and all the Keys, published in 1849, “Indian Key is not called Matanzas but instead Indian Key.”

Indian Key was a popular destination for several reasons, hence the Bahamian name for the island Kay Comfort. Located approximately midway along the Florida Reef, the island provided a fairly deep natural harbor, freshwater was accessible nearby on Lower Matecumbe and perhaps most attractively, because of its position, the island had a reputation for remaining relatively mosquito free. There was a time, in fact, when Indian Key was a veritable island respite featuring a hotel, bar and 9-pin bowling alley! 

In addition to being the site of the infamous Indian attack of August 7, 1840, the island has served as a U.S. Navy depot, a military hospital, farm, fish camp, the county seat of Dade County and home to the notorious wrecker John Jacob Housman. 

In an article published in the 1871 edition of Harper’s New Monthly Magazine, Dr. J.B. Holder described Indian Key in his piece “Along the Florida Reef” as, “The grand rendezvous for the wreckers, fortunately for us was near at hand. Indian Key is one of the few islands of the Reef that can be called inhabited. Here for many years the wreckers have resorted, as it is convenient as a midway station and the safest harbor in heavy weather. The whole island seems to have been under cultivation. Fine cocoa palms and many flowering shrubs are here, and what with the several houses the place looks quite village-like and picturesque.”

According to the 1870 U.S. Census, the original Pinders, Richard and Sarah Pinder, were living and farming on the island. By the time the 1880 census was taken the Pinders had relocated to Upper Matecumbe. Henry Flagler would buy the island in 1905 and Indian Key became the temporary location of the railroad’s Central Supply which utilized the island’s deep natural harbor. Wharves, too, were built to support dredge operations during construction of the train’s tracks.

During the Prohibition years, the island was reportedly used by rumrunners transporting liquor between the Bahamas and Miami. When the Great Labor Day Hurricane of 1935 devastated the Upper Keys on September 2, Ernest Hemingway, who had been living in Key West at the time, packed his boat Pilar with emergency supplies and motored north to Islamorada. He described Indian Key as, “…absolutely swept clean, not a blade of grass, and over the high center of it were scattered live conchs that came in with the sea, craw fish, and dead morays. The whole bottom of the sea blew over it.”

Now, while I live on Plantation Key and my favorite place to eat excellent fare while sipping cold rum is Key West, my favorite island to talk and write about is Indian Key. Several months ago a producer for The Florida Channel, Mike Licquia, visited the island to produce a piece for the program Florida Crossroads — Ghost Towns of Florida

Several ghost towns from around the Sunshine State are shown in the piece. Indian Key, however, is the feature. Park Ranger Marty Dillis was invited to offer insights into the history of the island and did a fantastic job. I was also invited. To watch the program and learn more about what is perhaps the most interesting island in the chain visit:

Brad Bertelli is a published author of four books on Florida and Florida Keys history. He is the curator of the Keys History and Discovery Center, located at the Islander Resort. His column will appear every other week in The Reporter. Reach Brad with comments and questions at