From railroad to overwater highway: Driving the spectacular route through the Florida Keys

People wandering down to spend a little time in the Florida Keys often end up staying much, much longer. “Thirty-one years ago, I came here on vacation,” said Eric Johnson, a tour guide on tiny Pigeon Key. Johnson met a guy in Miami on a Thursday who said he could come sleep on his couch in Marathon. “On Saturday morning, I was here.” He left for the winter, came back in the spring and has lived in the Keys ever since. He’s far from the only local who’s dropped in for a visit and ended up staying for decades. With views of Florida Bay on one side and the Atlantic on the other, the allure of this island chain is easy to see as you drive south into the Keys. But it’s the Overseas Highway itself — the 113-mile-long engineering marvel under your tires with the ghost of a railway whispering below — that’s allowed motorists to answer the call of the Keys for nearly a century. This is no blank-slate stretch of asphalt — the route, leapfrogging from one key to the next over 42 bridges, has seen tragedy and more than its share of colorful characters. Along this part of US 1 from mainland Florida to Key West, you’ll find relics of a historic railroad and plenty of ways to make the most of the aquamarine water all around you. Driving straight from Miami to Key West can take about four hours if things go smoothly. But if you’re beelining down to Mile Marker 0, you’ll be missing out. “I think people are learning more about the joy of the other Keys,” said Will Keizer, a captain at Captain Hook’s Marina and Dive Center, which has three locations in the Keys. “If you want bar-to-bar-to-bar busy, Key West is your jam — no doubt about it,” said Keizer, who’s originally from Michigan and has lived in the Florida Keys for about eight years. But “if you want to slow down, take in the sights,” he says, it’s time to explore beyond Key West. Here are some stops along the way. Under the surface Key Largo — the largest of the Keys and the first destination along the route — immediately delivers the underwater riches that bring divers here in droves. For wreck divers, the 510-foot Navy dock landing ship USS Spiegel Grove now serves as an artificial reef six miles offshore. Local dive shops run trips to the wreck, where sea turtles mingle with coral, sponges and cascades of colorful fish. (And for seafood lovers, the pink-orange hogfish fries up nicely at The Fish House). Also on Key Largo at Mile Marker 103, John Pennekamp Coral Reef State Park — the first undersea park in the US — offers snorkeling and scuba trips and glass-bottom boat tours. Down the road another 11 miles in Tavernier, the Blond Giraffe bakes up several delicious variations of the famous key lime pie, made from the zesty little limes that were once grown here commercially. ‘Flagler’s folly’ Drive on and you’ll soon find yourself in Islamorada, a community stretching across five inhabited islands. Just east of US 1, near Mile Marker 82, a monument to the victims of the 1935 Labor Day Hurricane serves as a reminder of the tragedy that cost hundreds of lives and spurred the creation of the new highway. Among the more than 400 dead were hundreds of World War I veterans who were working on a section of the Overseas Highway. Extensive damage from the hurricane put an end to a railroad dating back to 1912, the first direct, over-island route to Key West. “The state wound up taking over the railroad right of way and essentially made that rail line … a new version of the highway,” said Corey Malcom, lead historian at the Florida Keys History Center in Key West. “And that opened in 1938 and was connected by bridges. And people could then, from 1938 on, drive straight through from the mainland all the way to Key West.” While the Keys’ railroad chapter has long-since closed, reminders of the ambitious project are visible along the route, and its stories are told in exhibits throughout the islands. The Over-Sea Railroad was part of the Florida East Coast Railway, owned by Standard Oil partner Henry Flagler. The extension to Key West — inspired by plans for the Panama Canal and its trade possibilities — was dubbed “Flagler’s folly” by skeptics, but the first train reached Key West on January 22, 1912. After the 1935 hurricane hastened the railway’s demise, the railroad bed was used for the new road and some of the railroad bridges were converted for cars — narrow, white-knuckle affairs that live on in memories, in ruins and in a span that’s recently been revived as a pedestrian and biking path. Feeding the fish Continuing south along US 1 in Islamorada, you can’t miss Robbie’s on Lower Matecumbe Key — a one-stop compound for kitschy souvenirs, sport-fishing charters, cold drinks, hot meals and a tarpon feeding frenzy. For $2.50 you can access the dock and another $5 buys a bucket of fish to feed the tarpon. (For a quieter feeding atmosphere, Bud N’ Mary’s, a couple miles before you hit Robbie’s, doesn’t charge admission to its dock.) Some daredevils will let tarpon, which can grow up to 8 feet long, gulp their hands to the wrist for a great video moment, but Robbie’s visitors on a relatively quiet day in March were dangling fish through holes in a net, seemingly reluctant to participate in any unnerving limb gulping. Also in the menagerie was a manatee named Samantha and an aggressive flock of pelicans poised to snatch fish not promptly gobbled up by the tarpon. And policing the dock with a padded stick to maintain order was Ron Hauter, a Robbie’s employee whose right hand showed signs of tangling with the critters. At the time, Hauter, who had just moved down from Crystal River, Florida, was two weeks into his dream of living in the Keys. Florida native Carl Hiaasen, a novelist and former Miami Herald reporter and columnist, had the same dream growing up in Broward County and lived it for about nine years before he sold his house on Lower Matecumbe Key. But the island chain has served as the backdrop for some of his satirical crime novels, including “Bad Monkey,” which recently became an Apple TV+ series starring Vince Vaughn. “I’ve set several novels in the Keys because I still find it an intriguing place, not just for the natural beauty, but for the people — the characters — it’s attracting … You have an outlaw component, who’s drawn to the Keys, and you have dreamers, and you have families, and you have retirees and … just retired scoundrels,” Hiaasen said. Traffic snarls are one reason why Hiaasen ultimately returned to eastern Florida. The Upper Keys can be “a parking lot on the weekends,” he said. But for each resident who gets fed up with some of the hassles of Keys life, there’s someone like Ron Hauter ready to give it a shot. “Everything here is beautiful,” Hauter, 20, said enthusiastically. “The wildlife is so active — and aggressive. Everything is so aggressive in the Keys — I love it.” A traffic jam Plan B Regular traffic can be fierce along Route 1 — and when there’s a wreck? Well, with essentially one road in and one road out, it’s good to have some flexibility. Case in point: A Monday afternoon accident on the Seven Mile Bridge — the longest and most impressive modern span in the Florida Keys — snarled traffic for hours in early March. Fortunately, the Turtle Hospital, at Mile Marker 48.5, required less than a mile of backtracking, and a planned overnight in Marathon allowed for leisurely waterfront dining instead of hauling down to Key West, feeling hours behind schedule. The Turtle Hospital rescues, rehabilitates and, in many cases, releases sea turtles brought in because of boat strikes, disease and other hurdles encountered by the five species found in local waters. The 90-minute guided visit involves turtle education, a look at the medical facility and an outdoor tour to see (but not touch) turtles awaiting release as well as others deemed too vulnerable to live in the wild. Marathon, a community of 13 islands, also offers casual waterside dining where marine wildlife adds to the ambiance. Castaway features a sushi roll with lionfish — the restaurant’s effort to help rid the Keys of the invasive species. And the manatees jostling in the canal for a sip of cool water dripping from an air-conditioning system keep diners very much in touch with the aquatic environment. Over on the Gulf side of Marathon, Keys Fisheries offers order-at-the-window seafood, a full bar and waterfront seating with sunset views and glimpses of the sharks, tarpon and pelicans that patrol the marina. Old Seven Down the highway, near Mile Marker 47, the old Seven Mile Bridge — nicknamed “Old Seven” — is a prime place to get out and explore on foot. A 2.2-mile section of the old railway bridge, which was converted for highway traffic in the ‘30s and used until a new bridge was completed in 1982, reopened in 2022 to pedestrians and cyclists. At the end of the repurposed section, you can access Pigeon Key, a tiny island where hundreds of railway construction workers lived from 1908 to 1912. Admission is $15 for adults arriving on their own via Old Seven or $28 for those who opt to ride a tourist train from a parking lot a few miles back. Admission includes a guided tour, and you can picnic, snorkel and fish while you’re on the island. The railway construction workers toiled six days a week, 70 to 80 hours per week for $1.50 per day, according to guide Eric Johnson. There’s a small museum dedicated to their work on the island and several original buildings. Walking back on the paved pedestrian stretch, with traffic zipping along the wider Seven Mile Bridge nearby, you can see the eras of this route’s history. When the railway was first converted into a highway, the tracks were removed and a 22-foot sheet of steel was laid down and paved. The old train tracks became railings on either side. The narrow highway eventually earned the nickname “Highway of Mirrors,” according to Pigeon Key history, because cars passed so close to one another that their side mirrors were knocked off, littering the road. Time stands still Back in the car, after crossing over the newer — technically 6.79-mile — Seven Mile Bridge, history buffs will find another impressive railroad ruin: the old steel truss Bahia Honda Bridge. Today, the area around the bridge at Mile Marker 37 is part of Bahia Honda State Park, where a trail follows the route that was once US 1 up onto the old bridge, where you can walk on one section. Snorkeling trips run from the park out to Looe Key, a protected reef about 9 miles southwest of the park. Captain Hook’s also runs expeditions to Looe Key. At Looe, an hour spent floating above colorful parrotfish, angelfish and barracuda brings time to a near-standstill. Bobbing on the ocean’s surface, the value becomes clear of slowing down, breathing deeply and soaking up the pleasures of the other Keys. Some 30 miles down the highway, Key West awaits — with its rollicking bars, rooster soundtrack, Jimmy Buffett lore and historic sites tied to Harry S. Truman and Ernest Hemingway. But you should resist the urge to race to Key West straight from the airport in Miami or Fort Lauderdale, says Cori Convertito, a curator and historian at the Key West Art & Historical Society. “You’re going to get to Key West,” she said. “Hopefully Key West isn’t going anywhere anytime soon — so take your time.” Delight in the journey.