There’s something almost magical about driving from Key Largo to Key West along the famous Overseas Highway. In December 2025, we experienced this iconic 113-mile stretch of U.S. Route 1, and it lived up to every bit of its reputation as one of America’s most scenic drives.
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A Road Built on Dreams and Determination
The Overseas Highway has a fascinating history that makes the drive even more meaningful. Before this engineering marvel existed, Henry Flagler had an audacious vision: to connect the Florida Keys by railroad. His Overseas Railroad, completed in 1912, was considered one of the greatest engineering feats of its time. Flagler’s dream was to create a direct rail link from the mainland United States all the way to Key West, opening up commerce and tourism to these remote islands.
Tragically, the railroad’s glory days were short-lived. On Labor Day in 1935, one of the most powerful hurricanes ever to strike the United States devastated the Keys and destroyed much of the railroad infrastructure. Hundreds of lives were lost, and the railroad never fully recovered. In a remarkable turn of fortune, the state of Florida purchased the railroad’s remnants for just $640,000 and embarked on an ambitious project to convert the railway route into a highway.
The transformation was completed in 1938, and the Overseas Highway opened to vehicles. Initially, drivers had to pay tolls at booths on Big Pine Key and Lower Matecumbe Key—$1 for automobiles plus 25 cents per passenger. These tolls remained in place until April 15, 1954, when the highway became free to travel.
The Journey: Sun, Clouds, and Sea
Our December drive treated us to the full range of Florida Keys weather—a dynamic mix of clouds, brilliant sunshine, and passing rain showers. This ever-changing sky only added to the drama of the seascape surrounding us. One moment we’d be driving under brooding clouds with rain spattering the windshield, and the next, sunlight would break through, illuminating the turquoise waters on both sides of the road.
The highway features an impressive 42 bridges that connect the keys, each one offering breathtaking views of the Atlantic Ocean on one side and the Gulf of Mexico or Florida Bay on the other. As we island-hopped our way south, we passed through dozens of keys, each with its own character and charm.
The Crown Jewel: Seven Mile Bridge
Without question, the highlight of the entire journey was crossing the Seven Mile Bridge near Marathon. Though technically 6.79 miles long, this magnificent structure feels even longer as you drive across it with nothing but water visible in every direction. It’s an exhilarating experience that makes you feel like you’re driving across the open ocean itself. Once nicknamed “the eighth wonder of the world,” the bridge absolutely deserves its fame.
What made the experience even more intriguing was seeing the old Seven Mile Bridge running parallel to the modern one. These remnants of the original 1938 highway (which itself was built on Flagler’s railroad foundations) stand as ghostly reminders of the route’s layered history. Throughout our drive, we spotted several of these older bridges alongside the current roadway—some partially demolished, others still standing as fishing piers or historical monuments. They serve as tangible connections to the past, allowing us to imagine what travelers experienced decades ago.
A Living Legacy
The Overseas Highway underwent major improvements in 1982 when 37 original bridges were replaced with wider, stronger spans to accommodate modern traffic and hurricane evacuations. In 2009, the highway received special recognition as Florida’s first and only All-American Road, a designation reserved for routes with exceptional scenic, historic, and cultural significance.
Driving the Overseas Highway isn’t just about getting from Point A to Point B—it’s about experiencing a journey that floats between sky and sea, bridging history and modernity, connecting isolated islands into a unified paradise. Whether you encounter sun, clouds, or rain along the way, this drive remains one of America’s most unforgettable road trips.
So Many Stops, So Little Time
With 113 miles connecting dozens of keys, the Overseas Highway offers countless opportunities to explore. Over the years, we’ve discovered some memorable stops—and we’re already planning which ones to revisit and which new ones to add to our list.
A few years back when we went down for a boat ride through Biscayne National Park, we stopped at Robbie’s in Islamorada to feed the tarpon, those massive fish that can grow up to eight feet long. It should have been thrilling—you purchase a bucket of bait and hold the fish over the water, waiting for a tarpon to leap up and engulf it along with part of your arm (they don’t bite). But the pelicans had other plans. These aggressive birds were absolutely relentless, diving and stealing bait – we each attempted to feed the tarpon and Justin came tantalizingly close to success but drew away at the last minute. We watched other visitors battle the same feathered pirates. This trip, I considered stopping again to redeem ourselves, but we decided to keep moving to get to Key West while it was still light.
One stop that absolutely exceeded expectations was the Turtle Hospital on Marathon Key. The guided tour was incredibly informative, detailing the numerous threats these gentle creatures face—from boat strikes to plastic ingestion to fishing line entanglements. The staff’s dedication to rehabilitating injured turtles and providing permanent sanctuary for those unable to return to the wild was genuinely moving. The stories were heartbreaking enough that I nearly adopted a turtle, and we’ve been religiously avoiding plastic straws ever since.
We’ve also explored the Keys’ craft beer scene at two excellent breweries in Islamorada. Both Islamorada Brewing and Florida Keys Brewing Company offered quality brews and welcoming atmospheres, though we gave the edge to Florida Keys Brewing Company for their bright, spacious outdoor seating area. On this 2025 trip, we returned for lunch and discovered an incredible food truck serving tacos that were so phenomenally delicious, we couldn’t stop talking about them. We were already planning our return visit on the way back—only to find the truck closed. That disappointment might just guarantee another Keys trip in our future.
Still on Our List
While we’ve made two trips down parts of the Overseas Highway, there are still stops calling our name for next time. Bahia Honda State Park on Big Pine Key is renowned for having some of the best natural beaches in the entire Keys, with opportunities to swim on both the ocean and bay sides. The Dolphin Research Center on Grassy Key offers interactive programs where you can meet dolphins and sea lions up close. For history buffs, Pigeon Key—accessible by walking or biking part of the old Seven Mile Bridge—provides fascinating insights into the railroad workers’ lives during the bridge’s construction. And John Pennekamp Coral Reef State Park in Key Largo, America’s first underwater state park, promises world-class snorkeling and diving among vibrant coral reefs.
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