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A Florida Keys adventure: touring mysterious Indian Key

The Island Runaways have escaped to the Upper Keys many times, but one destination here we've never explored is mysterious Indian Key. Located in the Islamorada Village of Islands, accessible only by boat or kayak, this 11 acre island may look small, but it contains a wealth of Florida Keys history. Today, Indian Key is a state park, and as you'll find if you visit, there are signs throughout the trails giving you a sense of the events that transpired here, some over a century ago. But Zickie, our littlest Island Runaways member, and I were exceptionally fortunate today, because our tour guide was none other than Florida keys historian and writer Brad Bertelli. Even for independent-type travelers, this kind of expertise truly makes the past come alive.

Indian Key

(The boat dock at Indian Key. Photo by Island Runaways.)

We started out this morning, at Robbie's Marina in Islamorada, a popular destination for tourists with its restaurant, souvenir stalls, huge tarpon who love to be handfed, fishing charters, and of course, kayaks. The very nice guys at the Kayak Shack set up with with two double kayaks, and soon we were on our way on the beautifully clear and very calm ocean. One aspect of this activity we appreciated? You don't need to be super fit or an experienced kayaker to make the journey. Granted, it was helpful to have tour guide Brad leading the way and regaling us with history as we crossed toward Indian Key.

Island Runaways

(A beautiful morning kayak in the Florida Keys. Photo by Island Runaways/Z.A.)

We brought ashore our kayaks (so they would not float off) and soon we were plunged back hundreds of years. Historians believe that Indian Key derives its name from the fact that Indians once used the island as a base of sorts -- although some folks mistakenly believe that Indian Key gets its name from the massacre that occured here in 1840. But I'm getting ahead of the story. Brad explained that this small island has been strategically significant since Bahamian sailors used to call it "Kay Comfort." Before the keys had bridges or roads, this was a convenient place to take a break from a long sea voyage, particularly due to its natural, safe harbor at the time. Not far off, on the Matecumbes, there were sources of fresh water, an absolute necessity and something that has always been in short supply among these Florida islands.

Indian Key tours

(Our guide Brad Bertelli, who wisely wore a hat. Photo by Island Runaways/Z.A.)

An intrepid soul named Silas Fletcher first settled here in 1824, and opened a general store. Why have a store in the middle of nowhere, an uninhabited isle? As Brad continued to explain, Indian Key was an ideal stopping-off point for boats sailing down to Key West, at the time the only settled outpost and port for hundreds of miles around. Because so many ships ran aground against the Florida Reef, wrecking became a huge industry in this part of the world. With the general store installed, settlers began to move and build homes here.

Florida Keys history

(Indian Key had streets in its hayday. Photo by Island Runaways/Z.A.)

Eventually, a notorious wrecking captain, John Jacob Housman, who was based in Key West, took note of this burgeoning community. He realized that he could set up his own miniature empire here, a wrecking port-of-call to rival Key West. Gradually, with great cunning, he began to stake his claim and brought his wife here. Historian Brad has done extensive research on Indian Key and particularly on Housman, and showed us sketches and maps from the period. At one point, there was a hotel and bowling alley, right here! The descriptions, including stories from private diaries kept by residents of this lonely island, conjured up what life might have been like, before motor boats, cell phones, bottled water, or air conditioning. I can't possibly fit in all the fascinating details we heard as we wandered the (thankfully) shaded paths, but believe me when I say that even our eleven-year old was enrapt. More than enrapt, in fact, she had plenty of questions!

Smith & Sturdy Cottages)

(Cisterns and ruins of two cottages. Photo by Island Runaways/Z.A.)

We saw the foundations of a three story warehouse where Housman kept the valuable goods he would sell for mega profits. There are also remains of cottages throughout the island, and the three story home of Dr. Perrine, who was killed by Seminoles during the infamous attack of 1840. During this period, Indians and white settlers were vying for access to land and resources throughout Florida, with the Indians being driven further and further into the wilderness of the Everglades. Our tour guide sent chills down our spines as he recounted how, early on the morning of August 7th, residents awoke to find dug-out canoes lined up upon the shore. At the end of the invasion, seven settlers were dead, and Indian Key was in flames.


(A vista from Indian Key. Photo by Laura Albritton.)

Indian Key was never the same again. Today the island is something of a ghost town, although perhaps the prettiest ghost town you'll ever visit. Waterbirds flit into the tops of mangroves, while small lizards scamper in the brush. Stunning, turquoise water greets you at every turn. If you climb the observation tower, you get a lovely view of the entire island and surrounding scenery. Despite its tumultuous past, Indian Key today is a beautiful refuge, a natural treasure that has been perserved for everyone to enjoy. In addition to the paths and history you can learn, there's also great snorkeling around the island, so don't forget your masks and snorkels.

Of all the activities and attractions the Island Runaways have discovered in these southern islands, this was certainly one we'll never forget. As we kayaked back to Robbie's, with backward glances at mysterious Indian Key, I pondered how adventuresome those 19th century families must have been to settle here and try to make their lives on a remote outpost. Why would they come here? Why take the risks and endure such solitude? The reasons must be complex, but one motivation was crystal clear: because of the remarkable beauty.

For more information on Indian Keys tours, click on Brad Bertelli's website. If you venture out to the island, it's a good idea to bring water and possibly snacks, since the general store that once existed is long gone! Also, normally you will need to pay cash ($2.50 per person) for the entrance fee, in an honor system box, but if you come on Brad's historical tour he covers that charge for you.

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