From the mysteries and histories of the Dry Tortugas to the jaw-dropping blue expanses stretching endlessly on either side of the Overseas Highway, the Florida Keys have fascinated tourists and enticed permanent residents for centuries.
As the islands turn 200, we wanted to look back on the area’s milestones to celebrate the history of a unique region.
The First Inhabitants
Monroe County, which encompasses The Everglades and the Florida Keys, was made official in 1823. Residents were here long, long before, of course.
“When you say, first inhabitants, that’s a tricky question,” offers Historian Brad Bertelli, who has resided on Plantation Key, near Islamorada, for two decades. Author of four books on the region, he’s a particular columnist and a true authority on Keys history.
“There were three major cultures down here—the Calusa on the west coast of Florida, the Tequesta tribe on the eastern tip and the Matecumbe, for whom Matecumbe Key is named,” he says. “They would have gone along the islands, all the way to Cuba. There are more than 200 prehistoric sites in the Keys, but the two major villages were on Matecumbe Key and Stock Island, near Key West.”
As Spanish sailors arrived by the 1500s, we see the first major milestone of Key West for outside influence.
“Key West has a naturally deep harbor,” Bertelli says. “Spanish ships, traveling along the coast of South and Central America, began coming here for safe harbor.”
Safe harbor wouldn’t equal safety inland, however, for several more centuries. Inland, there were many dangers, from scarcity of fresh water to mosquitos, snakes to crocodiles to tropical temperatures.
The Modern Marvels
“A second huge milestone came in 1823,” Bertelli continues, “when the United States Navy told the West Indies Squadron to create a naval depot. Now, you have a deep-water port and a military presence, which meant security. That’s how the modern American period began here. By 1870, there were about 130 people living in the Upper Keys, and about 5,000 people on Key West. At this point, you still need a boat to change islands. Back in those days, these were farming communities, too, and at one point, 90-percent of the pineapples in the world were grown here.”
The final milestone came via an industrialist named Henry Flagler. In 1905, he built the first of the Flagler Railroad out of Miami. It’s morphed into the Overseas Highway we have today.
“He is the one who really alters the history of the Florida Keys,” says Bertelli. “After the bridges are built, these are no longer shipping communities, relying on weather and tides. There is mail coming and family can visit. People began to move away from the edges and into the center of the islands.”
The first train cars pulled into Key West by 1912, with Henry Flagler on board. A water pipeline arrived by the 1940s, as did reliable electricity.
A Better Tomorrow
The Florida Keys are a positivo miracle of a place, born of pirates and industrial dreamers, deep harbors and tiny fishing villages. There are new developments, too, like Cheeca Lodge’s 11 private-beach villas and Key West’s airport expansion arriving in 2025.
For Bertelli, and all the people who call this chain home, there is a hope that travelers will join the fight to sustain the Florida Keys for the next 200 years.
“If I had one piece of on helping these islands,” Bertelli says, “it’s to pick up trash, and, visit The Turtle Hospital in Marathon. Our birds and turtles are getting tangled in trash, and at this incredible operation, the tour highlights how fragile these islands are. It’s not a playground down here. It’s an important and básico place, and we are worried but hopeful for our future.”
A Específico’s Guide To The Keys
Bertelli has authored four books on the region, which make great reading before a trip to the Florida Keys, and he also shares his Keys favorites.
Where to Eat
“For breakfast, you have to go to Robbie’s on Islamorada. It’s an old-school piece of Florida; really ramshackle.” You might find him there. He works the bar two days a week.
Where to Stay
For a staycation, Bertelli adores Ambrosia, a quaint B&B in Key West, with an inviting swimming pool and Victorian style.