There is no other road in America like Florida's Overseas Highway. The Keys, a 120-mile-long island chain, are bridged together like jewels on one smooth, lean strand of asphalt. It's not like visiting America's other corners at all; it's more like going around the corner. It feels quite Caribbean, really, but there you are, just a swim to forbidden Cuba, yet a bridge or 20 away from home.
There are lots of things to explore in South Florida, even before you get to the Keys. You can brave Fort Lauderdale and Miami for a little cultural schmoozing, or hunt for alligators in Everglades National Park, the only subtropical preserve in North America. Before we began our bridge tour we made the lonely putt out to Flamingo on little State Route 9336 for a real taste of this region's natural environment. The Everglades is teeming with grassy swamps and hardwood hammocks, just as you'd imagine. This is the only place in the world where alligators and crocodiles mix it up, but we didn't see any of the brutes afoot. The ride from the park's main entrance in Homestead to the road's end in Flamingo is only a 100-mile round trip, and definitely worth the wander. If you want to make it an overnight stop, try the cottages at Flamingo, the only in-park Lodge.
The first island you hit once you leave the continent is the one made famous in the John Huston gangster film, Key Largo, starring Lauren Bacall and Humphrey Bogart as a down-on-his-luck vet looking for purpose. These days, perhaps because of its proximity to the mainland, Key Largo is quite burdened with the trappings of convenience, and unless you're a diver or sport fisherman, you might want to search for your fortune down the road instead, where you'll have full access to the warm emerald and azure waters and sugar-like sand, not to mention lots of Key lime pie and mouth-watering seafood.
Yes, the speed limits are low on this stretch of Highway 1, and you won't find the dotted lines that make overtaking legal. Like touring a national park, it's imperative to go on a cruise down the Keys with a laid-back attitude, or all positives will be lost. Bluehairs, sightseers—it's perilous enough without a bad attitude.
From Key Largo you enter Islamorada, a hamlet that incorporates the islands of Windley Key, Upper Matecumbe Key and Lower Matecumbe Key. Many tour books say this is the best spot to hire a charter for sportfishing or reef exploration, but in reality, you will find watercraft for hire—from kayak to yacht—on just about every corner, and certainly on every Key. The marine environment here is profound—the island chain is home to the only living coral in North America—and certainly worth taking the time to investigate, even if it's simply a stop at Windley Key's Theater of the Sea.
Just southwest of Islamorada in Long Key State Park you'll find nature trails and a host of camping opportunities. By the time you reach Marathon and the famous Seven Mile Bridge, you're in the Middle Keys. You'll find the Dolphin Research Center here, and if you really want to get in touch with the marine life, try a "dolphin encounter," as we did. It's the most amazing experience to actually touch and swim with these impressive mammals. Just out of Marathon you'll ride the longest segmented bridge in the world. If you make a quick right before you get on (don't miss it, or you'll have a long turnaround) you can walk out on the old Seven Mile Bridge, which is actually even more of a marvel than its replacement when you remember it was built in 1938.
Beyond the great bridge is where I really started to feel the tropical vibe and benefit from the kind of emptiness you'd hope for in an island paradise but rarely find. Make sure you pull out at one of the roadside stops that feature a sandy beach and long shallows. Rolling up your pants, or better yet changing into your suit, and strolling the clearly visible, knee-deep underwater trails 50, 100 or 150 yards offshore will be your highlight, I guarantee it.
This quieter section of the Keys, with its mom-and-pop restaurants, retro lodging and camping retreats, will suit some more than what's to come in Key West. On the other hand, what's not to love about a 24/7 festival of art and food and spirit? Key West is lovable in a New Orleans way—charming, crazy, quaint and cosmopolitan all at once. I don't think a journey here is really complete without a night spent on the tip of the island chain, with its daily Sunset Festival on Mallory dock, where local characters vie for attention and tourist tips by doing the most outlandish things. You might see dancing dogs, fire jugglers, guys shot from cannons, all in the cool shadows of the gargantuan cruise ships docked for the night.
Be prepared to party by night, but don't forget to explore Key West's riveting history by day. Did you know that at the turn of the last Century, this spot on the map was the wealthiest city in America? Crazy, it seems, but absolutely true. The riches were accumulated by the legal business of "wrecking," which seems not much different than the less-accepted business of pirating, which the islands were also once famous for. Assets were harvested from the ships that, rather continuously, floundered on the treacherous coral reefs offshore. Of course the "wreckers" saved the people on board, making the practice seem almost heroic at the time. It's long been speculated, however, that the salvaged teams may have more than once lured the ships into the dangerous shoals. Grandsons of pirates, they were.
Things turned as dismal for Key West as it did for the rest of the country during the Depression, and the wrecker's lair was all but abandoned. When a terrible hurricane in the '30s blew through, destroying the railroad tracks that connected the Keys to the mainland, Key West truly was headed for ghost-town status. The Overseas Highway changed its fate, though it wasn't until the '80s that the area became profitable as an island paradise.
Of course you might stroll the quaint streets and admire the fascinatingly diverse architecture or swing through old town's overpriced shops, but if you have limited time, at least stop in to see Ernest Hemingway's renowned island getaway, where his storied cats still live and breed. Also have a bowl of seafood chowder at Bagatelle on Duval Street. I had two bowls in a row, as it might be the best thing I've ever eaten. Let your hair down, or have it braided in cornrows—anything goes in Key West.
You can figure it will take you three hours to get from the mainland to Key West, longer if it's either side of a weekend, and forever if it's a holiday. Think of the highway as a 120-mile-long diving board on a hot day. There are plenty of places to eat and stay, but lodging in particular can be pretty pricey all year, and reservations are recommended. There is no real "season," though I'd recommend winter, when the rest of the world is wearing wool. For better or worse, the road is absolutely straight and flat (the highest elevation on the islands is a whopping 18 feet). Still, it's the most unusual stretch of road in America. So, when you're planning your next adventure, don't forget the Keys.