Edit ModuleShow Tags
Edit ModuleShow Tags

Paddling into the Past

Kayaking through the Calusa Blueway reveals fascinating signs of an ancient culture.

Jim Freeman


Before his ship wrecked and murderous natives enslaved him, Hernando de Escalante Fontaneda was the child of prosperous Spaniards serving the crown in South America. His mother and father had established colonies in Peru, and by 1545 they were expanding the realm to Cartagena, an ancient seaside town in Colombia. Escalante was born there.

At 13, he was old enough to sail to Spain and earn his education. So, with a light pack and a small allowance of pure gold, he and other prominent Spaniards boarded a ship called the Howker. This ship was to deliver them from the savage jungle to the land of their countrymen.

Instead, it sank. Some drowned. The rest flopped onto the shores of an even more savage terrain—Lee County.

At that time, though, it wasn’t the land of strip malls, retirement condos and seasonal residents. It was the land of the Calusa, a powerful tribe of fierce warriors. When the survivors washed up, the Calusa killed everyone but Escalante, and there on the islands of Estero Bay, the American Indians held him captive for 17 years.

Four and a half centuries later, my girlfriend and I went kayaking into Calusa territory. I was curious whether any trace of this storied landscape remained, or whether Midwesterners had completely bulldozed, paved, Port Royal-ed and Lani Kai-ed it. From here, in modern Florida, it’s difficult to imagine thatched encampments of naked American Indians performing human sacrifices and Spanish conquistadors prospecting for the Fountain of Youth. By paddling the lagoons and rivers of the Calusa Blueway, would the ancient landscape reveal itself?

Certainly I would need to pick up some granola bars and bottled water from Publix for this kind of journey back in time. I would also need to find the right guide. So when I saw his name online, I called immediately.

“Hi, is this Calusa John?”


It was an early morning in late winter, a cool 65 degrees and climbing. The sky was Carolina blue and cloudless. We were near downtown Bonita Springs preparing to kayak down the Imperial River.

At the river’s edge, John Paeno (his friends don’t seem to call him Calusa John) and the co-owners of Calusa Ghost Tours keep a shop full of America Indian gear, some of which they unearthed, but most of which they crafted themselves from the same shell tools the Calusa would have used. They had a spear, some plant-fiber yarn and a woven loincloth more texturally similar to steel wool than silk.

We slid into our kayaks. Our leader this first day was not Paeno but his business partner, Aaron Thomas, a Southwest Florida native now in his second career. He’d traded bank mergers for a paddle. The river, as always, was lazy. In fact, the only bubbles we saw were a few deliberate burps rising from what we assumed was Sally, the river matriarch, a 9-foot alligator with whom everyone living along the bank seemed preoccupied.

“You seen any ’gators?” asked a retired couple walking their dogs. Nope.

The tour was 2.5 miles in—we paddled till we could hear the whir of Interstate 75 and saw power lines overhead—and 2.5 miles back.

A middle-aged man in a Michigan T-shirt sat on a bench overlooking the river in a mobile home park. “You see any ’gators?” Nope.

Thomas told us about the Southwest Florida childhood most residents here never had. How he’d go out and find American Indian artifacts, like pottery pieces and spearheads. In those days, the stuff was everywhere, just lying on the ground. The Horseshoe Keys in Estero Bay held a mythic allure as the “Indian fish traps.”

The sun flickered through Spanish moss. The water appears black, steeped by plant decay. I tried to imagine the scene as a young Calusa might. Without the rope swings and cottages. Without the concrete bridge that smells like bat poop. I pretended I had never heard of computers or the United States or cars, though I could hear them distantly. I asked Thomas which plants and animals would have been there 1,000 years ago. Almost none of them, he said.

In so many ways, Florida has been shaped by invasion.

Then a man with a silver mustache, jeans shorts and a burgundy T-shirt edged up to the river bank. He held his chin poised as though preparing to make a great speech. The corners of his mouth angled. His lips parted: “Seen any ’gators?”



The second day of kayaking promised to reveal more of the Calusa civilization—Paeno was our guide, and we were headed for the capital city.

Our route (up U.S. 41, left on Coconut Road, paddle a couple of miles) was different from Escalante’s, but the destination was the same. I would trod upon the spot where a young Spaniard came of age in servitude. Modernity, our understanding and perception of the present, has a way of asserting its supremacy over the past, which is distant, like some other Earth. I hoped visiting Mound Key, the forgotten seat of a thousand-year empire, would disabuse me of my sense of permanence.

The three of us—Paeno in his kayak, my girlfriend, Christina, and I in a tandem one—paddled out on a breezy Friday. Soon we were in the cool, sun-flecked belly of a mangrove patch. “I call this the Time Tunnel,” Paeno said. The only sounds were the ripples the boat made; the world was otherwise still.

After navigating through the tunnel, we were suddenly in open water. No sign of time travel, however: The Hyatt Regency Coconut Point Resort & Spa still rose aft, and there were coastal condos ahead. But if you squinted and looked away, you could pretend. And there was Mound Key, with a jumping pod of dolphins fishing off its shores.


The Calusa were expert fishermen, brave warriors, handy navigators and master craftswomen. Their civilization was so prosperous, their social compact so firm, that by the time Escalante crawled onto their beaches they had already been around for 1,200 years, at least.

Calusa territory extended roughly from the 10,000 Islands to Charlotte Harbor and inland halfway to Lake Okeechobee, but their empire was much larger. All the tribes from Key West to Cape Canaveral paid taxes to the Calusa king; admission to the empire required payment in the form of one daughter.

They had other quirks. If the king’s child died, everybody had to kill their own children. If the king died, they butchered the slaves. And once a year they killed a Christian captive. The Calusa god fancied eyeballs, and they were eager to provide.

The problem for Escalante and his companions was the Calusa didn’t always follow the “just one annually” rule. They often massacred whatever sopping Spaniard washed up. Anybody who slipped away either hunkered down, Colonel Kurtz-style, or, more likely, baked to death in the forbidding glades wasteland. Escalante would occasionally encounter other shipwreck survivors. “It was a consolation,” he wrote in his memoir, “though a sad one, for those who were lost after us to find on shore Christian companions who could share their hardships and help them to understand those brutes.”

Why King Carlos, who ruled at that time from Mound Key, spared Escalante, nobody knows. Scholars assume it was because the boy was a deft linguist, and Carlos needed an interpreter. And so he was, living among the Calusa until he was 30, one of the longest captivities of any European in Florida, pre-air-conditioning.


In Calusa culture, artisans engraved their religious apparatus with images of dolphins. And while they ate most of the animals around them, they probably did not eat dolphins, or if they did, only the most important tribal leaders were allowed. The animals seemed different, somehow spiritually significant.

Paeno believes this, too. Sometimes when he’s fishing, dolphins come nearby. They’ve helped corral fish toward his kayak, and the dolphins appreciate Paeno because he always throws back his catch. Just once, a dolphin simply swam over and stared him in the eye.

The experience was “spiritual,” he said. “Like looking at an equal.”

Paeno is 57. He has long gray hair, which he ties back and covers with a floppy blue hat. He has a calm demeanor and says, “Can’t complain, I live in paradise” when you ask how he’s doing.

He wasn’t always Calusa John. In the beginning, he was an outdoorsy boy from Oswego, New York, a town built where the Oswego River drains into Lake Ontario. His father loved to sail. “I was raised on the water,” Paeno said. “If it floated, I was on it. A log, a raft, I didn’t care.”

He married his high school sweetheart, who happens to be American Indian, and became a manager at Fort Ontario in his hometown. “I’ve been interested in our past all my life,” he said. Going to work at a 19th century fort meant daily immersion in another time.

In 2003, he bought a place in Pine Island. “When I moved down here, I just kind of discovered artifacts,” he said. The Calusa made their tools from sturdy shells, and their pottery is the color of the sand. To the untrained eye, it’s easy to overlook a Calusa needle or bowl fragment. After Hurricane Charley, Paeno was among the first to take archeologists scouring the coast for uncovered relics, including Spanish gold the Calusa salvaged from shipwrecks. Though he’s not found gold, Paeno turns the objects over to the Florida Museum of Natural History. Eventually, they hired him.

Paeno still does historical consulting, sometimes paid, sometimes volunteer. But mainly he takes people kayaking and tells them stories about the people who used to live here. “I always feel there’s some kind of connection,” he said.

Jim Freeman


We dragged our kayaks onto a secluded beach and climbed to the top of Mound Key, a place where King Carlos likely held court with Escalante at his side.

Mound Key is not a natural island. Rather, it’s one of hundreds of examples of how the Calusa engineered their landscape. Those “Indian fish traps” really are Indian fish traps: The tide came in along with fish, then receded without them. Mound Key is 180 acres, constructed entirely of shells. There was a central canal that acted like a port through which visitors or attackers would have to navigate. Steep mound banks rose along each side, which was both intimidating for the guests below and useful for spear throwers above.

In his memoir, Escalante describes one day in the life of an interpreter on Mound Key. Paeno recounted the story:

When the Calusa captured Spaniards, they’d often order them to dance and sing. Of course, the Spanish had no idea what they were saying, so the Calusa would kill them for their rebelliousness.

Finally, King Carlos wanted to know what was up with those insolent Christians. “Escalante, tell us the truth,” he said, “for you well know that I like you much: When we tell these, your companions, to dance and sing, and do other things, why are they so mean and rebellious that they will not? … Is it that they do not fear death?”

“My Lord,” Escalante replied, “as I understand it … it is because they cannot understand you.”

By way of testing them, King Carlos commanded one group: “Se-le-tega.” Flummoxed, they didn’t budge. The king was convinced, and Escalante revealed the meaning of the word, which is, “Run to the lookout to see if there be any people coming.”

Escalante concluded: “They of Florida abbreviate their words more than we.”


Even on Mound Key, however, the modern world is not far. After Paeno related the Escalante story, we continued along the trail, which dips past a barbedwire fence containing a tribe of goats. (A group of goats really is called a tribe.)

The fence, the goats and the land are owned by three brothers named McGee—Tim, Todd and Ted—whose grandfather bought the property in 1914. As the rest of the island became a park, the McGees refused to sell their 10 acres for anything shy of $3 million. They’ve mounted a “FOR SALE” sign on the fence with a phone number.

I called the number and spoke with Todd McGee, an accountant in Fort Myers. He says there were 42 goats when I visited. Ten of them are now sausage. “They make great sausage,” he told me. And they’re great for clearing invasive plants.

Indeed, while I was there, a work crew was busy pulling weeds as part of a $26,000 project to eliminate anything that wouldn’t naturally grow on Mound Key. Which turned out to be almost everything. Their bare finished product looked a little like the McGees’ property, where the goats had done the job for free. McGee said the land is zoned “outer island,” meaning whoever buys it could build five or six houses there if they want to. (This fact is debatable.)

Despite the workers, goats and invasive plants, you can still make out the contours of the island. If I strained my imagination, I could almost picture American Indians hauling in the day’s catch or the Christian missionaries vainly hoisting crucifixes in the town square. But not long. Holding the picture in my mind’s eye was like trying to hold water in a colander.


Around 1569, Escalante was rescued. He finally made it to Spain and wrote his memoir six years later. Meanwhile, the Calusa held off as long as they could. They’d already killed Juan Ponce de Leon and maintained their way of life far longer than most other American tribes.

But by 1700, the Europeans were becoming more ubiquitous. The British were making gains against northern tribes, including the Creeks who fled south to Calusa territory. There were American Indian wars. The Creeks and their allies became known as the Seminoles. And when the British took Florida in 1763, the Spanish pulled back to Cuba with a group of 200 Calusa refugees—most of what remained of the once-great empire. Within a few months, every last Calusa fell ill and died in the foreign land. (There is, however, some speculation, by Paeno and others, that the Calusa bloodline continued in the Cuban mountains or in Oklahoma after the Trail of Tears.)

Paeno explained all of this as we made our way back up the 30-foot hill toward our kayaks. Then he stopped. He was holding a conch shell I hadn’t noticed before.

“In honor of the Calusa, I usually blast it three times,” he said.

He placed one hand on his hip and brought the shell to his lips. He exhaled, and out came a slow deliberate pitch, a middle G, like a trumpet stuffed with cotton balls. A conch filled with breath—whether Paeno’s or a Calusa shaman’s, now or 1,000 years ago—would make that same sound. No one can see the past, but suddenly I could hear it.

I asked whether Paeno believes in the Calusa religion. Not exactly, he said. “Energy never disappears. It always goes somewhere,” he explained. “We’re energy.” So it stands to reason that when we die, the spirit that animates us keeps going. “There must be a pool of energy somewhere.”

It was time to leave Mound Key.

We pushed off onto the water, then paddled until a pocket appeared in the mangrove coastline. Paeno called out: “Back through the Time Tunnel!”

His words were like a crack in a dam, and the whole world came rushing through.


Edit ModuleShow Tags

You Might Like

The Look: Blue Time

A hot watch in blue hue

A New Angel-a in Town

Angela Fine Furnishings has moved, gone public—and given us a great look to get our redecorating started.

Ending Soon: The Beatles at Southwest Florida Museum of History

Catch this exhibit in the 50th anniversary year of their famed appearance on the Ed Sullivan Show before it ends on Saturday.
Edit ModuleShow Tags
Edit ModuleShow Tags Edit ModuleShow Tags
Edit ModuleShow TagsEdit ModuleShow Tags
Edit ModuleShow Tags