The Weird, Wild Road Florida Road Trip Every Southerner Should Take

Discover the secrets of Overseas Highway.

I’ve always loved a road trip, that lovely suspension of real life, that time of being nowhere, when anything is possible and the whole future lies out before us like a dream. No place in the world is dreamier than the Overseas Highway (U.S. 1), the beautiful drive from the tip end of mainland Florida down the fabled Keys, my favorite journey in all the world. The flat turquoise water on both sides; those long bridges; the weird birds; the huge changing sky; those wild, brilliant sunsets. It’s always gorgeous, always surprising...and well, revelatory. You feel like you’ve been living in an old black-and-white photograph, and then a brighter future is opening up.

It’s technically 106 miles from Key Largo (Mile Marker 100 at the top) down to Key West (Mile Marker 1) on this legendary highway completed in the 1930s to replace Henry Flagler’s equally legendary railroad. Key Largo is justly famous for its tourist attractions such as glass-bottom boats, dive shops, and the John Pennecamp Coral Reef State Park (with its big underwater statue of Christ). Then drive on to Tavernier, where the road runs like a silver ribbon into the sky, Plantation Key, Upper Matecumbe Key, and Islamorada (renowned for fishing and the atmospheric old Cheeca Lodge).

Don’t miss the famous Green Turtle Inn, located in a cluster of wooden buildings at Mile Marker 81.2. This place has been popular since 1947, when people actually ate green turtle steaks processed at the nearby cannery. Inside, it’s just like walking into a  James Bond movie, with red leather barstools; dark wood throughout; a large, square bar; Dean Martin playing on the sound system; and walls covered in pictures of famous people (including Mickey Mantle and John Belushi). Sit down, open up the big leather menu, and order a margarita.

Forty-two bridges link the Keys, with most of them in the Middle Keys including the famous Seven Mile Bridge (mile markers 46 through 40), the longest stretch of road over open water there. It’s almost impossible to describe the sensation of driving across. It’s like you are transported to another country, a fabulous land of sky and sea, with the water spread out pale and shiny on either side of you to the farthest edges of the world.

Each Key has its charms, its secrets, its specialties, such as the National Key Deer Refuge on Big Pine Key, featuring the sweetest and most improbable little creatures I’ve ever seen with the biggest eyes. And Grassy Key’s Dolphin Research Center, where you can actually swim with them if you call ahead for a reservation. The Keys are filled with wonderful, almost fantastical animals—iguanas, pelicans, egrets, stingrays, manatees, ospreys nesting atop telephone poles. It’s like another world. It IS another world.

The people are pretty unusual too—artists, dreamers, dropouts, entrepreneurs, individualists. All are ready to help one another (or you) in an instant. Just check out some of these signs I spotted: “Crocodile Crossing,” “Psychic Oil Change and Gas”, “Go All the Way,” “Be Here Now,” “A Cool Congregation!,” “Your Wife Is Hot, Better Get Your AC Fixed,” and “Gator Heads and Wind Chimes.” And don’t miss all the manatee mailboxes. (I’d love to have one of those myself.)

Driving the Overseas Highway is a liberation from being the gravity-bound creatures we are—as well as a bridge to another world, Key West. It’s the place you come to be yourself, or maybe where you come to figure out who you are.

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