For many visitors, the Florida Keys are somehow detached from the rest of the state and easy to overlook. Geographically, that’s easy to understand as they hang down from the main peninsula like a pendulum, a string of vivid islands and islets that arc out into the Gulf of Mexico.
In many ways, they are more Caribbean than Floridian, with an ultra-laid-back vibe that totally suits this 113-mile-long tropical hideaway that ends up closer to Havana than Miami, and which offers one of the most scenic and captivating drives in the USA.
It’s called the Overseas Highway and it is an engineering marvel, an elevated road and series of bridges that connect each island in turn all the way to eclectic Key West, former home of Ernest Hemingway and a major tourist draw in its own right. It actually opened as Henry Flagler’s Over-Sea Railroad in 1912 and was hailed as The Eighth Wonder of the World, a stunning building achievement that extended Florida’s fabled East Coast Railway right through to the Keys.
Flagler’s bold dream was wrecked by the great hurricane of 1935, which devastated large sections of the railroad, and it fell into disrepair. The state took the opportunity to buy the whole route and convert it into one long road, which was completed in 1938, expanded in 1944 and modernised in the 1970s and 80s.
Now, it makes for a wonderfully scenic drive, from the southernmost Miami suburb of Florida City all the way to Key West, and it’s definitely something you should have on your radar as an opportunity to experience one of the most iconic features of the Sunshine State.
From Orlando, it’s a tedious seven-hour drive to Key West, but from Miami it’s a more manageable three-and-a-half, and it makes for a really compelling journey. We did the full drive this week, and here’s what we found.
The first major stop is this island-city made famous by the 1948 Humphrey Bogart-Lauren Bacall movie. It typifies the Keys’ low-rise, spread-out topography and boasts a long stretch of dual-carriageway to make the driving easy. Obvious highlights are John Pennekamp Coral Reef State Park, a thrilling opportunity to visit one of the world’s largest coral reefs by glass-bottom boat, snorkelling tour or scuba-dive, and Dolphins Plus Marine Mammal Responder, a combination of animal rescue-and-research centre and hands-on dolphin experience.
A short bridge across Tavernier Creek brings you to the next big island, or rather, a close-knit collection of six keys, where the landscape slowly starts to change, getting shorter and scrubbier as the land becomes narrower. You’ll still find plenty of residential areas mixed in with the resorts and inns, but this is where the real island terrain of the Keys starts to show. To get up close with it, you can take a tour with Paddle the Florida Keys, an excellent outfitter offering kayak and paddleboard tours into the local waterways and mangrove trails. Also here is the Theater of the Sea, a great place to see dolphins and sea lions, as well as turtles, stingrays, alligators and more, in an eco-friendly environment, and the funky Rain Barrel, a collection of local artists offering their wares at the giant lobster (yes, really, and it’s a great photo op). Stop at Robbie’s Marina for a real Keys moment where you can hand-feed the tarpon that swim there.
The last two sections of Islamorada – Upper and Lower Matecumbe – introduce the first of the large bridges that soar over the sparkling waters of Florida Bay, where the sea can be only a few feet deep and the colours span every shade of blue you can imagine. The 13 islands grouped together here, with the town of Marathon at the centre, are known for beaches and barrier reef, and they were hardest hit during Hurricane Irma last year, with some of their resorts – like the fabulous Hawks Cay on the islet of Duck Key – only just open again after all the damage. The Dolphin Research Center is another place to meet dolphins and more marine animals in an all-natural setting, while Crane Point features a tropical forest, bird rescue centre and natural history museum.
The bridges through Marathon become increasingly impressive until you reach the grand-daddy of them all, linking Hog Key and Bahia Honda Key. Seven Mile Bridge (or 6.7-Mile Bridge as it should more accurately be called!) is totally breathtaking, an immense span that passes Pigeon Key and just keeps going, flanked by a section of the Florida Keys Overseas Heritage Trail, part of Flagler’s original railroad bridge that has been converted into a pedestrian way. Bahia Honda State Park is also still recovering from Irma, but there are more colossal bridgeworks to admire as you head south, including massive Bahia Honda Rail Bridge (originally the railroad route, then topped by a roadway, but now just a relic) and South Pine Channel and Lower Sugarloaf Channel, which are both part of the Heritage Trail.
Finally, crossing from Boca Chica Key to Stock Island brings you to the southernmost city in the contiguous USA, Key West, with its attendant Naval Air Base and US Coast Guard Station. There is a lot to see here, and the best way to get a full overview is with the Conch Tour Train or Key West Trolley Tour, both of which highlight all the main sights and attractions, and allow you to get on and off all day for the same fee (Attraction Tickets Direct feature both, combined with luxury coach transportation from Miami in an excellent day trip here and here).
The Ernest Hemingway Home & Museum, Mel Fisher Maritime Museum, Truman Little White House, Fort Zachary Taylor, Key West Aquarium and Shipwreck Museum are all worth seeing, while you should definitely be in Mallory Square for the nightly Sunset Celebration, with live street entertainment and suitable adult libations to toast the occasion! It all adds up to an epic journey, supported by the constant backdrop of the aquamarine seas and the awe-inspiring scenery that goes with them.
It’s hard to sum it all up in just a few hundred words, so our best recommendation is just get out there – and get driving!
Want to know more about The Keys or any other aspect of a full Florida holiday? Come and ask your questions – or tell us your experiences – on the fab ATD forums.
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