Travel Guides

The Overseas Highway: A Classic Florida Keys Road Trip

By Lynn and Cele Seldon

As the southernmost leg of U.S. Highway 1 that’s often called the “Highway that Goes to Sea,” it remains a modern travel wonder and one of America’s classic drives. The magic carpet ride highway follows a trail originally blazed in 1912 when railroad baron Henry Flagler completed the extension of his Florida East Coast Railroad from Miami to Key West. The railway ceased operation after severe damage to its infrastructure in a 1935 hurricane and economic decline caused by the Depression-era. Completed in 1938, the highway’s foundation incorporated some of the original railway spans, as well as the coral bedrock of individual keys and specially constructed columns. The Overseas Highway represents a remarkable engineering feat: 113 miles of roadway and 42 bridges leapfrogging across the water from key to key in a series of giant arches of concrete and steel. The Atlantic Ocean lies on one side of the highway, with Florida Bay and the Gulf of Mexico on the other – providing drivers breathtaking vistas of open sea and sky. In 1982, 37 of the original bridges were replaced with wider spans, including the renowned Seven Mile Bridge (actually 6.79 miles long) at Marathon. In September 2011, after nearly seven years of construction, a rebuilt, safer $330 million road connecting the South Florida mainland with the Florida Keys was completed. The modernized “18-Mile Stretch,” a segment of U.S. Highway 1 between Florida City and Key Largo, features numerous safety, environmental, and aesthetic enhancements for those heading to the Overseas Highway and the Florida Keys. The project’s most iconic element, the 1.25-mile, 65-foothigh Jewfish Creek Bridge, was completed in May 2008 and has created an even more impressive, expansive visual driving approach to the Florida Keys. In 2009, the roadway was named an All-American Road, the highest recognition possible under the National Scenic Byways program established by the United States Congress. Today, drivers can leave Miami and travel the full length of the Overseas Highway, through all the Keys to Key West, in about four hours. However, trailblazing travelers should allow time to experience the natural beauty of the ever-changing land and sea bordering and framing the roadway, as well as sunrises and sunsets that can be viewed from the road. 

Mile Marker (MM) by iconic Mile Marker, the highway also is the foundation of the Florida Keys Overseas Heritage Trail, which is currently being created. The trail is a multi-use bicycle and pedestrian trail that is to extend 106 miles from Key Largo to Key West, as a recreational greenway for hiking, running, bicycling, inline skating, fishing, kayaking, and more. Florida State Parks officials project that 90 linear miles are to be completed by December 2018. 

The underwater life of the Florida Keys attracts snorkelers, divers, and other water sports enthusiasts. Following Hurricane Irma divers and dive operators off Key Largo quickly reported that long-favorite dive and snorkel sites located three to four miles offshore remained very much intact, despite some topographic changes and a displacement of sand from deeper waters into shallow areas of the reefs – which tidal cycles and ocean currents typically correct over time. Beloved dive and snorkel sites like Molasses Reef, “Christ of the Abyss” (a nine-foot-tall, 4,000-pound statue overlooking a still-thriving coral reef dominated by a giant brain coral), and world-renowned wrecks like the Duane, the Spiegel Grove, and The Benwood, all remain open for business. In fact, Key Largo dive operators – many of them Blue Star companies promoting marine conservation – have excitedly noted that the experience on some wreck dives is like seeing them for the first time. This provides yet another reason to hit the Overseas Highway. “Wherever you travel along the Overseas Highway when you journey to the Keys, you can expect a welcome as warm as our year-round subtropical climate,” says Stacey Mitchell, director of marketing for the Florida Keys and Key West. That welcome begins as you head from South Florida down the Overseas Highway toward Key Largo.

Key Largo

The jumping-off point to the Florida Keys is Key Largo, about 50 miles south-southeast of Miami and beginning at MM 107, running to 90). The longest island of the Keys chain, Key Largo is the site where Humphrey Bogart and Lauren Bacall battled both actor Edward G. Robinson and a hurricane in the 1948 feature film of the same name, celebrating its 70th anniversary this year. Portions of the movie were filmed at the Caribbean Club (MM 104) in Key Largo and Bogie’s Key Largo connection can be experienced aboard the historic steamboat, African Queen – the actual boat that Bogart skippered in the movie of the same name. (It’s docked at the Holiday Inn complex at MM 100 and its operators run great trips). Keys underwater conservation was underway in 1960, with the dedication of John Pennekamp Coral Reef State Park off Key Largo (MM 102.5), named for a late Miami newspaper editor who championed local environmental preservation. It opened in 1963. As the first such underwater preserve in the United States, this refuge offers 50-plus varieties of delicate corals and more than 600 different species of fish for the viewing pleasure of divers and snorkelers. Pennekamp and the adjacent Florida Keys National Marine Sanctuary cover about 178 nautical square miles of coral reefs, seagrass beds, and mangrove swamps. The land-based part of the park also features excellent hiking and camping. Operators inside the park offer scuba diving, snorkeling, and varied boating, to reopen in early 2018, and other outdoor recreation. Key Largo’s Reef Environmental Education Foundation (REEF) opened a new interpretive center and campus improvement project adjacent to its existing headquarters at MM 98 in December 2017. REEF is dedicated to conserving marine ecosystems worldwide and the new center highlights the marine world through selfguided exhibits and engages visitors through firsthand discovery and displays. Exhibits highlight Keys ecology; fish, invertebrates, and plants in marine habitats; biodiversity; invasive and endangered species; conservation actions; water quality; and climate change. The expanded REEF campus includes a walking trail with native plants, picnic tables, and outdoor educational signs.



Islamorada (stretching from MM 89 to MM 66) is the centerpiece of a group of islands known as the “purple isles”– the islands feature a heavy concentration of the stunning violet sea snail and “morada” is Spanish for purple. Also known as the “Sportfishing Capital of the World,” Islamorada is heralded for its angling diversity and features the Keys’ largest fleet of offshore charter boats and shallow water backcountry boats. According to the International Game Fish Association, the Florida Keys boast more sportfishing world records than any other destination on the planet. Here, anglers can find sailfish, marlin, dolphin (the fish, not the mammal), kingfish, snapper, barracuda, grouper, and more in the ocean. Tarpon, bonefish, permit, redfish, and other species thrive in the shallow coastal waters as well. Numerous highprofile figures, including past presidents and British royalty, have visited Islamorada to fish or compete in acclaimed fund-raising fishing tournaments. Marked by a giant lobster named Betsy out front, The Rain Barrel Village (“A Village of Artists,” MM 86.7) is a perfect place to go for Keys souvenir shopping. Other noteworthy sightseeing in the Key Largo area includes the fascinating Florida Keys Wild Bird Rehabilitation Center at MM 92. Further west, vistas of the Keys are dominated by emerald-green lagoons, deep-blue seas, nodding palms, rustling pines, and olivegreen mangroves. White herons, roseate spoonbills, pelicans, seagulls, ospreys and other creatures share this paradise with visitors. For fishing, shopping, tasty food, and a Keys-y vibe, it’s hard to beat world-renowned, Robbie’s Marina of Islamorada (MM 77.5). The Hungry Tarpon Restaurant at Robbie’s is a great place to try fresh tuna sashimi salad, local lobster, grouper, classic key lime pie, and more. Islamorada is also known for Theater of the Sea (MM 84.5), the second oldest marine mammal facility in the world, and the appropriately located and fascinating History of Diving Museum (MM 83). There’s also the bustling Morada Way Arts & Cultural District (MM 82) for unique gallery shopping and more.



Marathon, stretching from MM 65 to 45, is the heart of the Florida Keys and is home to Crane Point, a 63.5-acre attraction (MM 55) that is one of the most important historical and archaeological sites in the Keys. The area contains evidence of pre-Columbian and prehistoric Bahamian artifacts and was once the site of an entire Indian Village. There is a tropical palm forest and a freshwater pond, attracting neo-tropical migratory bird species. There are also six hiking trails, the Marathon Wild Bird Center, the Crane Point Museum and Nature Center, and the Adderley House. While it is discouraged to feed marine life in the Florida Keys Marine Sanctuary, visitors can swim with and feed the fish at busy Florida Keys Aquarium Encounters (MM 53.1). There’s also The Turtle Hospital (MM 48.5), a veterinary center dedicated to the “rescue, rehab, and release” of sea turtles – and open for public tours. It’s the only one of its kind in the world and the first licensed veterinary hospital dedicated to treatment and release of injured sea turtles. The Marathon area is also the home of Dolphin Research Center (MM 59), a non-profit mammal research and educational facility that houses a family of dolphins in natural saltwater lagoons. Here, dolphins of all ages share their lives with visitors and people who have dedicated themselves to maintaining the best possible environment for them and all dolphins. A wide variety of programs includes interactive dolphin experiences. Those hungering for Keys seafood and atmosphere will want to head to Keys Fisheries (MM 50). This famed restaurant and market are known for its giant lobster Reuben sandwich, but there’s much more on the menu, including stone crab when inseason (October 15 to May 15) and lots of fresh local seafood. A drive across the Seven Mile Bridge passes the five-acre Pigeon Key, a small island accessible only by ferry from the Faro Blanco Lighthouse at the Faro Blanco Resort and Yacht Club in Marathon. The island once housed 400 workers who built Henry Flagler’s Over-Sea railroad in the early 1900s. It was also a supply depot, a dormitory with commissary and a passenger train stop.

Lower Keys

Southwest of Marathon, the Lower Keys stretch from MM 45 to MM 4. The sheer sweep of the Straits of Florida and the Gulf of Mexico is readily seen from Bahia Honda Bridge (MM 38). Bahia Honda State Park, like Pennekamp and Long Key state parks, also features day use activities that include hiking, snorkeling, and a scenic Calusa Beach, adjacent to Bahia Honda Bridge, for sunbathing. Big Pine Key (MM 30) is noted for Looe Key Reef, an area of the Florida Keys National Marine Sanctuary located about six miles offshore, and serves as home to the 9,200-acre National Key Deer Refuge, protecting the endangered miniature Key deer, living only in the Keys. Popular nature tours by kayak or larger boats offer unforgettable opportunities to view the unique fauna and flora of the Keys. Bill Keough offers backcountry paddling adventures through his company, Big Pine Kayak Adventures (MM 30).

Key West

Key West

Few U.S. cities can rival Florida’s Key West for its character…make that characters. This colorful, quirky island – the southernmost point in the continental United States – has been home, sweet home to a passel of colorful, quirky characters who call themselves conchs after the colorful, hardy mollusks that thrive in the waters here. Ernest Hemingway, for example, left such a mark on Key West that exploring his old stomping grounds is reason enough to visit the island. “Papa” moved to Key West in 1931 with his second wife, Pauline. The couple has gifted the house at 907 Whitehead Street. by Pauline’s wealthy Uncle Gus. Standing at the typewriter – he had a bad back – Hemingway created parts or all of To Have and Have Not, For Whom the Bell Tolls, The Green Hills of Africa, A Farewell to Arms, and Death in the Afternoon. Hemingway is one of the world’s most famous authors and a Key West icon. The Ernest Hemingway House & Museum, now a registered national historic landmark, was built in the Spanish Colonial style of native rock hewn from the area. The Hemingways furnished the house with rugs, tiles, chandeliers, and furniture collected from all over the world. In 1961, Hemingway killed himself in Idaho. Today, the Key West house and its furnishings remain intact, as if Hemingway were about to return from an afternoon of fishing or drinking. Besides his simple study, left as he liked it for writing, two other things demonstrate that the home and Key West still belong to Papa. One is the shrubbery that the nature-loving writer planted and the other is the multitude of six-toed cats roaming the place – descendants of Hemingway’s own cats and a living link between the man and the island. A visit to the Hemingway house is obligatory for tourists. But, those who want to meet live Key West characters head for Mallory Square. If there is a single Key West attraction that sums up the entire island experience, it’s the nightly “Sunset Celebration.” Every evening, as the glowing orange sun sinks beneath the horizon, Key West’s colorful characters turn out to celebrate the colorful event. Legend has it that playwright Tennessee Williams started the tradition – gin and tonic in hand – when he lived in Key West. But Key West’s spectacular sunsets have been drawing gasps of admiration for centuries. A Key West sunset is much more than a natural phenomenon. It has its own nonprofit organization, the Key West Cultural Preservation Society, and a cast full of quirky characters who give it…character. On any given evening, visitors meet up with arts and crafts exhibitors, street performers, food sellers, and even psychics. It’s a multicultural mélange that has to be experienced to be believed. Artist and naturalist John James Audubon wrote glowingly of Key West’s spectacular sunsets when he arrived in 1832. After studying and drawing birds and plants in their Keys natural habitats, Audubon stayed at the 205 Whitehead Street home of Captain John H. Geiger, a salvager and harbor pilot. Each day, Audubon explored the mangroves in search of native birds and plants, sometimes starting at 3 a.m. and working into the following night. The house and gardens have been completely restored and now comprise a public museum called the Audubon House & Tropical Gardens. The majestic home features original hinges, hardware, and wood, as well as period furnishings and numerous engravings by Audubon, including many from his famous “Birds of America” folio. It is believed that Audubon sighted and drew 19 new species while visiting the Keys and the Dry Tortugas. The Key West Cemetery, with a monument to the U.S.S. Maine, is also filled with island characters. Situated on 19 prime acres in the heart of the historic district, the cemetery boasts tombstones inscribed with all sorts of odd, if witty, comments like: “I Told You I was Sick.” Key West conchs also seem to have a penchant for nicknames. Sharp-eyed cemetery snoops will find tombstones bearing monikers such as Bunny, Shorty, and The Tailor. Visitors will also uncover some colorful tales at the Mel Fisher Maritime Museum. Typical of Key West characters, the late Mel Fisher was the stuff of tall tales, a fortune hunter who prowled the world in search of treasures buried under the waves. The museum displays many of his finds, including part of more than $400 million in gold and silver from the Nuestra Senora de Atocha, a 17th-century Spanish galleon that sank just 35 miles west of Key West. The Key West Attractions Association, one of Key West’s oldest business associations, celebrated its 35th anniversary in late-2017 by unveiling its new 2018 Vacation Pass, with more than $1,000 in savings and value-added enhancements. The association’s 75-plus members include Key West attractions, tours, water activities companies, charters, resorts, restaurants and bars, and other businesses. Member Key West Aquarium, one of the region’s oldest attractions, opened in 1935 and promotes itself as the first aquarium to use an open-air concept in its design (today, the aquarium’s interior is air-conditioned). In addition, the new complimentary hop-on, hop-off Duval Loop bus service makes it easy to travel around the island’s Historic Seaport and downtown Duval Street without a car. Launched as part of Car-Free Key West and designed to promote healthier, eco-friendly alternatives to driving, the route on colorful pink and blue buses includes 16 stops and is designed to reduce traffic and parking challenges. Further afield, 70 miles west of Key West, Fort Jefferson National Monument in the 100-square-mile Dry Tortugas National Park offers one of America’s most unique outdoors outings. This former 19th-century fort, 30 years in the making from 1846 to 1875, was never finished nor fully armed. Reached only by boat or seaplane, the fortress is part of a protected national park that features great birdwatching, diving, snorkeling, camping, and even more Florida Keys nature in abundance. After all that exploring near and far, Blue Heaven is a classic Key West bar and restaurant for meeting local characters. Key West’s close connection with Cuba and its characters (including Hemingway) can also be explored (and tasted) at El Meson de Pepe at Mallory Square. With so much going for Key West, it’s not surprising that the island has captured the hearts of many who have visited, including President Harry Truman. The 2.27-acre presidential winter estate, a former U.S. Navy commander’s home, has come to be called the Harry S. Truman Little White House. After discovering Key West in 1946, Truman became so enamored of the island that he returned every few months during his presidency. In a letter to his wife, Bess, Truman wrote: “I’ve a notion to move the capital to Key West and just stay.” Key West as the capital of the United States? Ah, what a wonderful country that would be!

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