Overseas Highway

Considered a marvel of engineering when it was first constructed, the Overseas Highway connects Miami and mainland Florida to the Florida Keys. Originally stretching a total of 113 miles (182 km) with 42 oversea bridges, the highway was constructed over the bed of the Overseas Railroad, which was constructed by Henry Flagler as part of the Florida East Coast Railway. When much of the railroad was destroyed in a hurricane in 1935, the roadbed and bridges were sold to the state of Florida; thus, the Overseas Highway was completed in 1938 and gave motorists access to the multitude of coral and limestone islands that make up the Florida Keys.

While most of the Overseas Highway runs to the right of the original railroad line, some of the old bridges can still be seen as you drive along through the Keys. The portions where pedestrians are allowed are now popular fishing spots; historic bridges like the Bahia Honda Bridge and Long Key Bridge are now fishing piers.

The Highway as a whole is a destination of its own, affording views of impossibly aquamarine water, Robinson Crusoe-esque islands and plenty of examples of classic Florida kitsch in the form of roadside stands and mom-and-pop shops. The National Scenic Byways program named the Overseas Highway an All-American Road in 2009. It’s the only All-American Road in Florida and one of 30 in the entire country.