Traveling the Highway That Goes to Sea

The road unrolls like a long dark ribbon in front of the car, with immense vistas of turquoise water and paler blue sky stretching endlessly on either side.

Driving from mainland Florida down the Overseas Highway, it’s easy to understand why the southernmost leg of U.S. Highway 1 is often referred to as the “Highway That Goes to Sea.”

In fact, from Key Largo to Key West, the 113-mile road incorporates an astonishing 42 bridges over the open waters of the Atlantic Ocean, Florida Bay and the Gulf of Mexico. From the top of some of the larger spans, particularly in the Upper Keys, the individual islands in the sprawling Keys chain look tiny and fragile against the sea and sky.

Yet despite their small size, these islands support lively, picturesque communities. The highway winds past Upper Keys marinas housing sportfishing fleets and sailing yachts, oceanfront villas surrounded by palms and flowering plants, enticing seafood restaurants and resorts both upscale and funky.

“Cruising” further down the highway, with passing miles marked by small green signs on the road’s shoulder or median, the tang of salt air wafts in through the open car windows. The Upper Keys, including Key Largo and Islamorada, give way to the Middle Keys and Marathon, a family-friendly community whose top draws include charter fishing and environmental attractions like the unique Turtle Hospital.

Just southwest of Marathon lies the undisputed jewel of the Overseas Highway: the Seven Mile Bridge. Driving across the 6.79-mile span over blue water, you realize why the original bridge was nicknamed “the eighth wonder of the world” after its completion in the early 1900s.

Yet the Seven Mile Bridge wasn’t always a highway bridge — and the Overseas Highway wasn’t always a road. It began as a railroad, the brainchild of millionaire Henry Flagler, who envisioned a train route connecting all the Florida Keys and mainland Florida. Flagler inspired an army of men to spend seven years constructing the railroad’s bridges and land-based tracks, and in 1912 the first train pulled into Key West.

After only two-plus decades of carrying freight and wealthy vacationers, much of the railroad was badly damaged in a 1935 hurricane. Three years later the Overseas Highway debuted, built on a foundation that incorporated some of the original railway spans.

In 1982, 37 original bridges, including the Seven Mile Bridge, were replaced with wider ones. Today, drivers see many of the old bridges stretching alongside their modern counterparts. Some have become popular sportfishing piers. Chief among the original bridges is the Old Seven Mile Bridge, a weathered expanse of majestic arches and cracked roadway that parallels the new bridge — though its center span has been removed to allow boat traffic. Once a vital link between islands, it’s now a walking trail leading to Pigeon Key, a pocket-sized island with a restored railroad camp and museum showcasing Flagler’s achievement.

Past the bridge, the scenery becomes wilder and more deserted. This is Big Pine Key and the Lower Keys, a realm of small communities, ecotourism and wildlife refuges created to protect species including the miniature Key deer. Beautiful Bahia Honda State Park and the Old Bahia Honda Bridge beckon to the left of the road, inviting exploration.

Eventually the Lower Keys segue into Key West, where the highway ends amid 19th-century charm and contemporary attractions. The ambiance of continental America’s southernmost city — situated closer to Cuba than Miami — is embedded in its quaint, palm-shaded streets, century-old gingerbread mansions, superlative sunsets and flourishing creative community.

It is, of course, possible to leave Miami and travel the entire length of the Overseas Highway, through all the Keys to Key West, in less than four hours.

But veteran Keys travelers know a hurried approach is not the way to experience this laidback destination. Take it easy. Experience the true flavor of each region of the Florida Keys. Take pleasure in the ever-changing land- and seascapes to be viewed from the “Highway That Goes to Sea.”