Many visitors to the Florida Keys find themselves ensnared by the region’s charm, often extending their stay far beyond their initial plans.
Eric Johnson, a long-time tour guide on Pigeon Key, recalls his own vacation that turned into a lifetime commitment.
“Thirty-one years ago, I came here on vacation,” he said, reflecting on the fateful encounters that led him to Marathon, Florida, where he has settled down since then.
The drive to the Keys, with the breathtaking views of Florida Bay on one side and the Atlantic on the other, is an experience filled with its own magic.
The Overseas Highway, a remarkable 113-mile engineering feat, facilitates this journey, allowing motorists to traverse from mainland Florida to Key West.
For nearly a century, this highway—a ribbon of asphalt connecting a series of islands—has witnessed both tragedy and colorful histories, stories often connected to the ghosts of a historic railway that once ran through the area.
While driving straight from Miami to Key West generally takes about four hours, those who skip the stops along the way miss out on rediscovering the joy of less-traveled parts of the Keys.
Will Keizer, a captain at Captain Hook’s Marina and Dive Center, encourages travelers to explore beyond the lively atmosphere of Key West for more tranquil experiences.
Key Largo, the largest and first island on the route, is a key destination for divers eager to unveil its underwater beauty.
A notable wreck site, the USS Spiegel Grove, serves as an artificial reef six miles offshore, where avid divers can encounter sea turtles and vibrant marine life.
Local dive shops offer organized trips to this fascinating dive site, which contrasts with the culinary delights at The Fish House, known for its excellent hogfish dishes.
John Pennekamp Coral Reef State Park, also on Key Largo, has garnered fame as the first undersea park in the U.S., with snorkeling, scuba trips, and even glass-bottom boat tours available for visitors.
As one travels further down the highway, Tavernier offers another tempting treat—the famous key lime pie at the Blond Giraffe, made from the tangy limes that were once cultivated commercially in the region.
Moving into Islamorada, a community spread across five inhabited islands, visitors encounter a significant historical monument commemorating the victims of the devastating 1935 Labor Day Hurricane.
This storm claimed more than 400 lives, many being World War I veterans laboring to extend the railroad that would eventually become the Overseas Highway.
Corey Malcom, the lead historian at the Florida Keys History Center, elaborates on how the hurricane’s aftermath saw the railroad’s conversion into a highway system that opened in 1938, connecting Key West directly to the mainland.
History enthusiasts will see reminders of the once great railroad still dotted along the route, with exhibitions narrating its ambitious story.
The railway was part of the Florida East Coast Railway, initially envisioned by Henry Flagler, who faced skepticism regarding its feasibility—dubbed “Flagler’s folly.”
Despite doubts, trains first reached Key West in January 1912, only for the hurricane to hasten its decline and prompt the highway’s creation.
The old infrastructure of the railway still provides a window into the past and continues to intrigue those journeying through the keys.
In Islamorada, one cannot miss the kitschy Robbie’s on Lower Matecumbe Key, a bustling place filled with fishing charters and the opportunity to feed large tarpon for a small fee.
For some, the thrill of letting a tarpon nibble on their hand is too enticing to resist, while others prefer a slower pace away from the action.
Ron Hauter, a staff member at Robbie’s, shares his enthusiasm after moving to the Keys, expressing his love for the vibrant wildlife:
“Everything here is beautiful.
The wildlife is so active — and aggressive.”
Meanwhile, celebrated Floridian novelist Carl Hiaasen, who once called Lower Matecumbe Key home, also reflects on the unique appeal of the Keys, describing them as a melting pot of intriguing characters and stories.
Despite the allure, Hiaasen notes that traffic can be a frustration, describing the Upper Keys as a “parking lot on the weekends.”
For those who seek the beauty of the Keys but also an escape from congestion, alternatives abound, such as the Turtle Hospital at Mile Marker 48.5, a short detour offering a meaningful experience.
The Turtle Hospital works tirelessly to rescue and rehabilitate sea turtles that encounter various threats, from boat strikes to disease.
Guided tours provide educational insights into turtle conservation efforts, while the chance to see turtles awaiting their return to the wild enhances the experience.
Marathon, a sprawling community of 13 islands, delights visitors with waterfront dining that showcases rich marine life against picturesque backgrounds.
Castaway offers innovative sushi rolls featuring lionfish, promoting local efforts to combat this invasive species through their menu.
Diners can enjoy views of manatees and other wildlife, creating a unique waterfront dining experience.
Continuing along the highway, the old Seven Mile Bridge entices visitors to break from their vehicles for a leisurely stroll.
This 2.2-mile span of the former railway bridge reopened for pedestrians and cyclists in 2022, allowing guests to access Pigeon Key and explore its rich history.
Once a home for railway workers from 1908 to 1912, this tiny island still offers insights into the rigorous work life of its inhabitants and features a small museum dedicated to their memory.
Walking back along the paved path, one can observe the evolution of this highway’s history, from its narrow, perilous beginnings to modern times.
A relatively short drive from the old to the new Seven Mile Bridge leads to the Bahia Honda Bridge, an impressive remnant of the railroad still captivating visitors at Mile Marker 37.
Bahia Honda State Park offers beautiful trails and access to snorkeling adventures at nearby Looe Key, where vibrant underwater ecosystems thrive.
During a snorkeling trip, the wonders of the ocean come alive, highlighting the wisdom in taking time to slow down, breathe, and appreciate the natural beauty surrounding the islands.
Ultimately, the journey culminates in Key West, brimming with lively bars, iconic roosters, and a rich historical tapestry related to notable figures like Harry S. Truman and Ernest Hemingway.
However, historian Cori Convertito reminds travelers to relish the journey itself:
“Hopefully, Key West isn’t going anywhere anytime soon — so take your time.”
Traveling the Keys invites everyone to savor the picturesque landscape and experiences each stop has to offer, transforming a simple travel plan into a memorable adventure.
image source from：https://wsvn.com/news/local/florida/from-railroad-to-overwater-highway-driving-the-spectacular-route-through-the-florida-keys/
