This 113-Mile Overseas Highway Connects Florida To The Keys Using 42 Bridges

If you've ever looked at a map of southern Florida, you've likely had a thought along the lines of, "Hey, the Keys look really far away. Is it really possible to just drive there?" Well, you sure can, thanks to the whims of real estate developer and Standard Oil cofounder Henry Flagler — the train enthusiast who gave us the Overseas Highway. (Today's Florida trains are faster but more deadly.)

The Overseas Highway wasn't originally a highway at all. It was first conceived and ridden as a railway over 113 miles of water, like a Jimmy Buffett-themed take on the sea railway from "Spirit Away" or the sea train from "One Piece." But in 1938, three years after a storm destroyed many of the rails, the U.S. government stepped in to rebuild the bridges for car use instead — the Over-Sea Railroad became the Overseas Highway, and visitors to the Keys were finally able to drive the hours to Key West instead of taking in all that pesky view out the side windows. 

I've actually ridden the Overseas Highway as far as Plantation Key, the second of the Keys, and let me tell you: It sure is a highway. The bridges pass over some truly beautiful water, the islands have gorgeous vegetation, but the road is just that — a road, mostly with one lane in either direction (the above image shows a rare four-lane section). There isn't room to pull off and take in the scenery between the Keys, and pulling off on an island only greets you with the sights of a combination KFC-Taco Bell.

The Overseas Highway is an engineering marvel, though it doesn't contain the longest stretch of U.S. highway with no exits, which, of course, is also in Florida. But it doesn't give drivers much of a chance to stop and smell the roses. That makes perfect sense for a railway, where nearly everyone on board is a passenger, but the 1938 conversion to passenger car use cemented these gorgeous bridges as simply things to be passed over — a route to a destination, rather than destinations in themselves.

That's probably what Henry Flager would have wanted, as the owner of the resorts at the far end of the highway. But it's a shame for those of us who love looking out over the long, gorgeous stretches of water that the Overseas Highway runs through.