Every time I make my way south along US 1 in the Florida Keys, I find myself dreaming about sitting at anchor in the beautiful blue water behind one of the many islands.
At the same time, I wonder how many of those islands have been home to someone.
Perhaps an ancient Indian tribe, or some hardy pioneer, putting down roots long before Henry Flagler ever thought of building a railroad through Florida.
For today’s adventure in the Keys, I paddle a kayak from Robbies Marina out to Indian Key alongside Brad Bertelli, a local historian and guide. He knows this island better than most. And he has made it his personal quest to learn as much as he can from the aging historians of the northern Keys.
We paddle into a small cove and pull our boats up on the shore, joining a few others who are exploring the island. To my surprise, from the beach we come to a neatly kept path with hand made street signs. Walking to the dock, I realize that these paths seem to be in a grid on the island.
At the dock, I find an “Iron Ranger,” the small lockable drop boxes for leaving fees while visiting unmanned State Parks and facilities. It made me chuckle. I never would have expected to need cash while visiting an island by kayak. But Indian Key is also Indian Key State Park.
Brad walked me through the island and its long history. In the early 1700s, one of the ships in the Spanish treasure fleet was wrecked on the Florida reefs by a hurricane.
The survivors camped on this Island until they were rescued. Later, the island would be used as as a base camp for fisherman, turtle hunters, and loggers.
Indian Key was not permanently inhabited until the 1820s. By the 1830s, there was a thriving community. In 1836, it became the county seat of the newly formed Dade County.
A court house was built and a post office soon followed. The thriving town eventually had a three story warehouse, a two story hotel, two stores, and dozens of individual residences. Only Key West was a larger outpost in these islands.
After the start of the Second Seminole War, most of the Keys were abandoned by pioneer settlers. Only the people of Key West and Indian Key remained.
Cannons were brought to the island, and a small militia formed to protect the island and its residents.
On August 7, 1840, a band of Indians snuck onto the island. Luckily, a resident sounded an alarm and most of the people living on the island escaped.
The Indians set fire to the town, and killed a half dozen people, including one prominent resident, botanist Henry Perrine.
For the next century, hurricanes erased what was left of the abandoned town. Only the rubble of stone foundations, a couple of gravesites, and several large cisterns remain.
The pathway around and through the island leads you to the remains of many of these early structures. Each has an interpretive sign.
Near the center of the island, the Florida Park Service erected an observation tower, giving you a rare view of the island from above.
Walking back to our kayaks, I could only imagine what life was like for those living here. Cut off from the mainland of Florida, with only boats for transportation.
This was a pioneer life that I had never given much thought to.
It was an easy paddle back to Robbies Marina. This was my first kayak paddle in the Keys and it was beautiful.
And a very pleasant surprise to learn so much history about a little 11 acre island that thousands of people drive past daily, with no idea that there is a ghost town only a short paddle away.
If You Go
Indian Key is located offshore from Lower Matecumbe Key in Islamorada. It can only be reached by boat. Arrange for a kayak rental at Robbie’s Marina. There is a $2.50 per person state park admission fee, payable at the dock. The island is open during daylight hours only.
Learn more about Brad Bertelli’s Indian Key Walking Tour
Rent your kayak at Robbies Marina