From Railroad To Overwater Highway: A Florida Keys Road Trip

Felix Dubois

5 min read

Post on Apr 28, 2025

4.6

Share

A Historical Journey: From Railroad to Highway

The Overseas Highway, a marvel of engineering, wasn't always a roadway. Its story begins with Henry Flagler's ambitious Overseas Railroad, a feat of construction that extended the Florida East Coast Railway across the Florida Keys at the beginning of the 20th century. Henry Flagler's legacy is deeply intertwined with the development of the Keys, and his railroad opened up the region to tourism and commerce. However, the 1935 Labor Day Hurricane devastated the railroad, leaving much of it in ruins.

The construction of the Overseas Highway, which we enjoy today, began as a response to this disaster. The "Overseas Highway construction" project was a monumental undertaking, requiring innovative engineering solutions to overcome the challenges of building across the ocean. This undertaking cemented the legacy of Henry Flagler's visionary railroad project even further.

• The challenges faced during the construction of the Overseas Highway: Building over water presented immense logistical and engineering difficulties, including dealing with strong currents, hurricanes, and the inherent instability of the Keys' geography.
• The significance of the 7 Mile Bridge: This iconic bridge, with its stunning views, is a symbol of the Overseas Highway and a testament to human ingenuity. The 7 Mile Bridge offers breathtaking views and is a must-see for any Florida Keys road trip.
• Interesting historical facts and anecdotes: Learn about the workers who risked their lives to build this incredible highway and the stories behind some of its most iconic landmarks.

Key Largo: Your Starting Point

Your Florida Keys road trip begins in Key Largo, the largest of the Upper Keys. Key Largo offers a plethora of activities to kick off your adventure. Known for its exceptional diving and snorkeling opportunities, Key Largo is a paradise for underwater enthusiasts.

• Exploring John Pennekamp Coral Reef State Park (snorkeling, diving): Discover the vibrant underwater world of the only living coral reef in the continental U.S., snorkeling or scuba diving. Key Largo diving offers unforgettable experiences.
• Enjoying water sports like kayaking and paddleboarding: Explore the calm, shallow waters at your own pace.
• Relaxing on the beaches: Bask in the Florida sunshine on the beautiful beaches of Key Largo.
• Finding great seafood restaurants: Indulge in fresh, delicious seafood at one of Key Largo's many waterfront restaurants.

Exploring the Middle Keys: Islamorada & Marathon

Continuing your Florida Keys road trip, you'll reach the Middle Keys, home to Islamorada and Marathon.

Islamorada, known as the "Sport Fishing Capital of the World," is a haven for anglers. You can book Islamorada fishing charters to try your luck at catching some of the region's prized game fish. Beyond fishing, you can also visit the Theater of the Sea or the Dolphin Research Center.

Marathon offers a more relaxed atmosphere. Here you can visit the Marathon Turtle Hospital, dedicated to the rehabilitation of injured sea turtles, or explore the beautiful Bahia Honda State Park. Bahia Honda State Park camping offers stunning oceanfront sites. Don't miss the spectacular views of the Seven Mile Bridge from Marathon.

• Casting a line for a thrilling fishing experience: Book a charter or try your hand at pier fishing.
• Visiting the Turtle Hospital: Learn about the incredible work being done to save injured sea turtles.
• Exploring Bahia Honda State Park's pristine beaches: Relax on white sand beaches and take a refreshing dip in the ocean.
• Enjoying breathtaking sunsets over the ocean: The sunsets in the Middle Keys are truly spectacular.

Reaching the End: Key West & Beyond

The culmination of your Florida Keys road trip is Key West, a vibrant city with a unique character. Key West is famous for its laid-back atmosphere, vibrant nightlife, and rich history.

• Witnessing the iconic Key West sunset: Don't miss the daily sunset celebration at Mallory Square.
• Exploring the Ernest Hemingway Home and Museum: Discover the life and work of the famous author.
• Wandering down Duval Street's lively atmosphere: Experience the vibrant nightlife and eclectic shops of Duval Street.
• Taking a boat trip to Dry Tortugas National Park: Explore this remote national park with its historic fort and pristine coral reefs (plan ahead, as boat trips require reservations).

Key West offers so much to do; from snorkeling to exploring its many historical attractions like the Ernest Hemingway Home and Museum, your days will be full of activities. Be sure to plan for enough time in this remarkable city!

Conclusion

From its fascinating history as a railroad to its present-day status as a breathtaking overwater highway, a Florida Keys road trip offers an unforgettable experience. Whether you're a seasoned traveler or a first-timer, this journey promises stunning scenery, thrilling activities, and a rich cultural experience. So, pack your bags, and get ready to embark on your own unforgettable Florida Keys road trip! Plan your adventure today and experience the magic of this iconic highway for yourself. Don't delay – your perfect Florida Keys road trip awaits!