As I was gliding for miles between the shimmering waters of the Atlantic Ocean and the Gulf of Mexico, seagulls were squawking above my head. The blue sky seemed to descend into the sea, and the water had turned turquoise due to the shallows between the coral and limestone islands.
As I adjusted my sunglasses, I caught a blurry glimpse of something moving out of the corner of my eye. A dolphin with a bottle-like nose! And it had friends with it. I looked over, and the group performed an aquatic ballet. They made an arch-like jump before disappearing into the waves.
Fishing boats were slowly circling around me, and I wanted to watch them, but driving at 50 miles per hour on the highway made it difficult.
The journey from Miami to Florida’s Key West Island hasn’t always been as easy as it is today. In the early 20th century, the only way to reach the southernmost point of continental America was a day-long boat ride, subject to the whims of weather and waves.
But thanks to an engineering marvel known as the Overseas Highway, which stretches 113 miles across 44 tropical islands via 42 bridges from the southern tip of the mainland, this journey has become a pleasure.
As I drove across it, I felt as if I were floating between mangrove forests and coral reef islands. I arrived at the point where North America meets the Caribbean islands.
The Overseas Highway actually started as the Overseas Railroad, a brainchild of visionary developer Henry Morrison Flagler (known as the father of modern Florida).
In 1870, Flagler co-founded the Standard Oil Company with business magnate John D. Rockefeller, which became one of the largest and most powerful corporations in the world by the beginning of the 20th century. After visiting Florida and recognizing its potential for tourism, Flagler invested most of his wealth in the region.
He built luxurious resorts that transformed one of America’s poorest states into a winter haven for Gilded Age travelers from the northeastern United States. Yet, there was no way for guests to reach Flagler’s grand but remote resorts.
So, in 1885, Flagler connected a series of railroads along Florida’s Atlantic coast, linking Jacksonville in the state’s north to Miami near its southern tip.
The rail line was supposed to end in Miami, but when the United States began construction on the Panama Canal in 1904, Flagler saw tremendous potential in Key West, which was the closest U.S. landmass to the canal and had the deepest port in southeastern America.
Thanks to the industries of cigars, sponging, and fishing, this bustling area was already thriving (Key West was Florida’s largest city by 1900), but the remote location made it difficult and expensive to move goods northward.
Thus, Flagler decided to extend his tracks 156 miles south to Key West, most of which lay over open sea. The so-called Key West Extension was considered an impossible project by many of his contemporaries, and his critics dubbed his vision “Flagler’s Folly.”
Three hurricanes between 1905 and 1912 wreaked havoc on the construction site, killing over 100 workers. But Flagler remained resolute and committed to his plan.
It took seven years and $50 million to build the railroad, requiring the labor of 4,000 African-American, Bahamian, and European immigrants. They braved alligators, scorpions, and snakes to accomplish this feat under harsh conditions.
When the railway was finally completed in 1912, it was hailed as the “Eighth Wonder of the World.” On the first train journey, a wood-fueled engine brought the rail from Miami to Key West, and the then-82-year-old Flagler stepped out of his private luxury carriage (which is now in the Flagler Museum in Palm Beach) and reportedly whispered to a friend, “Now I can die happy. My dream is fulfilled.”
Florida historian Brad Bertelli said, “The fact that Flagler funded [more than $30 million of] it out of his own pocket back then… Could Jeff Bezos or Bill Gates do that today? Elon Musk with his SpaceX is a modern comparison.”
The railroad operated until 1935 when the most deadly hurricane of the century washed away miles of its tracks. Instead of rebuilding, the idea arose to repurpose Flagler’s achievement for Americans’ newfound love of the automobile.
In 1938, the U.S. government began constructing one of the world’s longest trans-oceanic roads, relying on Flagler’s seemingly indestructible bridges. The highway was designed to withstand 200-mile-per-hour winds and storms.
Workers paved the way for cars over the tracks, and the newly minted Overseas Highway forever transformed the remote Florida Keys into a flourishing tourist destination that led to where it is today.
More than a century after the completion of the railroad, 20 of the original bridges still carry travelers from Miami to Key West. You can drive from one end to the other in less than four hours, but veering off course is part of the fun.
A charming series of under-the-radar stops forces travelers to appreciate how this engineering marvel was created and how it had a lasting impact on the Florida Keys.
Key Largo, 68 miles south of Miami, is the northernmost part of the Florida Keys and the first stop. Alligators, snakes, and other aquatic insects may have terrified Flagler’s construction crew, but now visitors come to Key Largo (self-proclaimed “Diving Capital of the World”) to marvel at this marine life.
Adjacent to John Pennekamp Coral Reef State Park, the Florida Keys National Marine Sanctuary attracts snorkelers and divers eager to immerse themselves in the only living coral reefs in North America.
The seagrass beds here provide an important habitat for fish, manatees (sea cows), and sea turtles, but the real attraction is swimming under the outstretched arms of Christ of the Deep, a 9-foot-tall bronze statue of Jesus that has been watching over visitors since 1965.
Once you’re dry, head to Islamorada, which lies halfway between Miami and Key West and was once the site of an Overseas Railroad station. At the Keys History & Discovery Center, a 35-minute documentary highlights the construction of the railroad and the many obstacles it faced.
The museum also displays artifacts from the golden age of trains, including dining items and an original menu listing roast beef for $1.60.
Between 1908 and 1912, nearly 400 workers lived in a camp on the tiny coral island of Pigeon Key, 35 miles south of Islamorada, while constructing the most difficult part of the over-sea railroad, the Seven Mile Bridge (colloquially known as Old Seven), which connects the Middle and Lower Keys.
In 1909, civil engineer William J. Krome was tasked with the difficult job of building a bridge over a 6.8-mile expanse of open water. Construction crews worked around the clock, trying to secure over 700 supporting piles in the middle of the ocean, sometimes plunging nearly 30 feet below sea level. They were assisted by divers who helped build concrete piers underwater to support the weight of the train tracks.
The remains of the old construction camp can be accessed by taking a trolley over the old bridge. The 2.2-mile section (the only part accessible) reopened in January 2022 after a five-year, $44 million restoration.
Closed to regular traffic, the bridge is now safe for those who want to bike, rollerblade, or observe marine life such as sea turtles and nurse sharks from 65 feet above the clear waters.
Pigeon Key currently has four permanent residents. The five-acre island is now a National Historic Landmark and is primarily powered by solar energy. There is also a museum offering guided tours of the various buildings, detailing what life was like for the crew during the construction of the Seven Mile Bridge.
Those who complete the entire journey on the Overseas Highway know they have reached the end when they see the Mile Marker in Key West.
The museum covers Key West’s 500-year history, showing how this seven-square-mile tropical island transformed from a pirate haven to a commercial hub and then into a tourist destination famous for its hospitality. Artifacts from the railway era include the paymaster’s car, which served as a kind of mobile bank to deliver salaries to railway employees.
The Eighth Wonder of the Modern World exhibit highlights the evolution of the railroad and explains how every obstacle was overcome by pushing the limits of early 20th-century technology.
Florida Keys historian and author Dr. Corey Convertito said, “If I had to name the most influential event in Florida Keys history, it would undoubtedly be the completion of Flagler’s Overseas Railroad. Through his vision, dedication, enterprise, and foresight, the Keys were connected to the U.S. mainland for the first time. It forever affected the path of the Keys’ economy and opened the doors to the tourism industry we see today.”
