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Indian Key holds intriguing Seminole connection, history

ISLAMORADA — The Florida Keys are well known as a place to destress, to kick back and relax, maybe go fishing, snorkeling or scuba diving – all while thinking about where you’ll grab a bite to eat and perhaps drink a beer or two as the sun goes down. You get the idea.

But that laid back and warm environment, like many parts of Florida, hasn’t always been the reality.

While historians agree the Keys were not a major battlefield area during the Seminole Wars, they were a part of it, and Indian Key – located about halfway between Miami and Key West – is one of the more intriguing sites where a significant attack took place.

The attack is often referred to as the “Indian Key Massacre.” It happened Aug. 7, 1840, and involved a number of lively characters, both Native and not.

“The interesting thing about [the attack] is the group that was involved [was] under the leadership of Chakaika,” said Dave Scheidecker, research coordinator and archeologist at the Tribal Historic Preservation Office.

Chief Chakaika, often misspelled as “Chekika,” was known as a fierce Seminole warrior.

Kayaking is one of the easiest ways to access Indian Key. Some people use canoes or paddleboards. The boat dock at site was damaged during Hurricane Irma and has not been fully repaired.
(Photo Sergio Tirado)

Scheidecker said while Chakaika’s group was part of a coalition that were the Seminole at the time – (there were many individual bands within the Seminole, from the Miccosukee and the Cow Creek, to the Tallahassee and the Black Seminole) – they were often referred to as Spanish Indians. There’s some confusion about what that means.

“There’s some evidence that this was a group with direct ties to either the Calusa or the Tequesta, survivors of them who had joined with the Seminole,” Scheidecker said. “There’s also evidence that this group had a lot of Spanish blood and were closer in culture to the Spanish.”

Scheidecker said there are records that the group were fisherman who regularly traveled between Cuba and Florida.

“Given the circumstances of Spain losing Florida (in 1819), there’s certainly good reason for them to have sided with the Seminole. It’s also known that the Seminole kept up trade, and it’s possible the Spanish Indians were the link to Cuba for the Tribe. It also explains why they would have good knowledge of Indian Key and the stores there,” Scheidecker said.

Indian Key, an island, in the Upper Keys. (Photo Sergio Tirado)

The ‘Massacre’

Historians say hostilities with the Seminoles on Florida’s mainland added to an increasing population on Indian Key. The 11-acre island had significant stores because it was known as a site with a busy wrecking operation, and it had fresh drinking water and other resources.

Chakaika’s band knew there was valuable bounty to be had.

Accounts say Chakaika came ashore with 60 to 130 warriors. The number of dead varies as well, from six or seven to upwards of 18 people. There is agreement that most of the structures on the Key were burned that day.

The “massacre,” which seems to be a term used by white men to describe any Indian attack, resulted in the death of an important figure on the Key – Dr. Henry Perrine, a physician and horticulturalist living there with his family.

Records say Chakaika’s group carried off “tons of loot and supplies” among the large stockpiles of salvage and other materials stored in warehouses.

The warehouses were owned at the time by notorious wrecker Jacob Housman, who was known to own most of the island.

Chakaika and his crew left with as many as 28 canoes and six of Housman’s boats filled with their bounty. They sailed and paddled about 90 miles back to what was known as Chakaika’s base hidden in the Everglades.

The raid was considered significant, in part, because it was an embarrassment to the U.S. Navy who had a depot only about a mile away on Tea Table Key.

Eventually Chakaika and many of his warriors would be brutally killed because of the raid – hung at the hands of Lt. Col. William Harney of the U.S. Army. The nature of their deaths was significant as it would enrage Sam Jones, one of the most influential Seminole leaders.

The Florida Keys History & Discovery Center is a great starting point to learn about Indian Key and many of Florida’s Indigenous People. It’s located about four miles from the Indian Key Historic State Park.
(Photo Sergio Tirado)

It seems to have fed more escalation of violence. “We have given them heretofore, when prisoners, a decent death, and shot them instead of hanging them like a dog,” Jones is quoted as saying. He promised “eternal hostility and cruelty” to his enemies after Chakaika’s death.

“Indian Key’s significance to the Seminole War is that the island demonstrates the desperate nature of the Indians and the steps they were willing to take to fight for what they believed,” said Brad Bertelli, the curator at the Keys History & Discovery Center and an expert on Indian Key.

“The attack on Indian Key was unique in the sense that the Indians traversed a great distance over water in order to attack, and it is one of the rare instances where the Indians used one of the island’s cannons to fire at American forces,” he said.

If you go

Despite its sometimes violent and bloody history, those who have studied Indian Key cite its natural beauty and encourage people to visit and learn more about it.

A Historic State Park since 1971, it can only be accessed by kayak, canoe or paddleboard. Its boat dock was damaged by Hurricane Irma and has not yet been repaired.

To get there, you can rent a kayak at the Kayak Shack at Robbie’s Marina in Islamorada. From Robbie’s docks it is about a 20 to 30 minute paddle in mostly shallow waters to the shores of Indian Key.

Once there, you will see remnants of many of the homes and warehouses that existed in the 1800s, as well as cisterns and other structures. The Key is home to a unique mix of plant life, due in part to experiments that were carried out by Perrine.

Plan to spend at least an hour walking around its well-maintained paths. There is good snorkeling off its north shores. There is a $2.50 per person State Park fee at the site.

Before you go, however, consider taking a trip to the Keys History & Discovery Center at the Islander Resort in Islamorada, where you’ll likely run into Bertelli.

Brad Bertelli is the curator at the Keys History & Discovery Center in Islamorada. He is considered an expert on Indian Key.
(Courtesy photo)

“We have a model of Indian Key – how it would have looked prior to the Indian attack,” Bertelli said.

In fact, Indian Key is Bertelli’s favorite subject. He’s written books about snorkeling in Florida and on other Keys-related topics, but he’s most excited about his forthcoming book on Indian Key and a mobile app he’s developing – Walk Indian Key – which should be available in May.

“For me, all of Upper Keys history starts with Indian Key. It is this little, seemingly no-nothing island that people drive by every day with no understanding of the vast history associated with [it].

“The island also serves as a monument to the Seminole War and offers the chance for historians to tell the story of the war — sadly uses of the word “massacre” and the white bent of the stories that are often repeated tell only one side of the story and by no means create a complete picture of what was going on at the time,” Bertelli said.

Major Indian Key dates

1775: The first time the name Indian Key appears on a chart. The chart used the Bahamian name for the island Kay Comfort.

1824: The first white settler comes to Indian Key and builds a general store.

1828: Thomas Gibson purchases a two-story home and the general store and begins to create the Tropical Hotel.

1830-1831: Wrecker Jacob Housman moves to the island.

1832: John James Audubon visits.

1833: Post Office first opens.

1836: Dade County formed and Indian Key becomes County Seat.

1838: On Christmas Day, Perrine arrives with his family. He has plans to create the Tropical Plant Co.

1840: On Aug. 7, Indians attack. There were approximately 50 people on the island at the time. (Bertelli thinks six or seven people were killed, depending on the account. Some documents do not account for one of the young boys who was killed – a black slave).

1870-1873: Indian Key becomes the base of operations for construction of Alligator Lighthouse.

1971: Purchased by the State of Florida and becomes Indian Key Historic State Park.

(Source: Brad Bertelli)

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Damon Scott
Damon is a multimedia journalist for the Seminole Tribune. He has previously been an editor and reporter for digital and print media in Florida and his home state of New Mexico. Send him an email at

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