Why You Should Visit the Florida Keys

When you’re looking for a major Florida road-trip adventure, look no further than the state’s crown jewel, the Florida Keys, and the fabled Overseas Highway.

Not only is this one of the most brilliantly eye-catching drives in the USA, it is a wonderfully historic part of the Sunshine State and an All American Road (like Route 66), that is rightly regarded as something extra special.

Now, it’s going to require a long drive from Orlando. Make that a LONG drive. It’s nearly 300 miles from our villa areas to Key Largo at the top of the Keys. That’s around four to five hours driving, and you’re going to need at least one overnight stay.

But it will be worth it. If you like driving in the US, you’ll LOVE the 98-mile stretch of Highway 1 from Key Largo to Key West, which constitutes the Overseas Highway.

For many visitors, the Keys are somehow detached from the rest of the state and easy to overlook. Geographically, they hang down from the main peninsula like a pendulum, a string of vivid islands and islets streaming into the Gulf of Mexico, as much Caribbean as Floridian, with a laid-back vibe that totally suits this tropical hideaway that ends up closer to Havana than Miami.

Why is it called the Overseas Highway?

Highway 1 is an engineering marvel consisting of 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. It opened as Henry Flagler’s Over-Sea Railroad in 1912 and was hailed as The Eighth Wonder of the World, a stunning achievement that extended Florida’s famous East Coast Railway right through to the Keys.

Sadly, Flagler’s creation was wrecked by the great hurricane of 1935, which destroyed whole sections of the railroad, and it fell into disrepair. The state took the opportunity to buy the complete 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 something you should have on your radar as an opportunity to experience one of the most iconic features of the Sunshine State.

Here’s what you find as you reach the Keys across scenic Blackwater Sound, and then head south:

Key Largo

The first major stop is this island-city made famous by the 1948 Humphrey Bogart-Lauren Bacall film. 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 with a hands-on dolphin experience.

Islamorada

A short bridge across Tavernier Creek brings you to the next main island, which is a 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 Village, 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.

Marathon

The last two sections of Islamorada – Upper and Lower Matecumbe – introduce the first 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 here, with the town of Marathon at the centre, are known for beaches and barrier reef, plus more natural facilities. 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 and Curry Hammock State Park adds a pristine, secluded hideaway with a dazzling array of birdlife, including migrating peregrine falcons each autumn.

Lower Keys

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 breath-taking, 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 was badly damaged by Hurricane Irma in 2017 but has bounced back better than ever, with its gorgeous views and palm-lined beaches. You will also discover more colossal bridgeworks 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. Next up is Big Pine Key, home of the National Key Deer Refuge and its super-cute miniature deer.

Key West

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, plus a great party vibe, especially at busier times of the year. There is a lot to see here, and the best way to get a full overview is with the Conch Tour Train or Old Town 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.

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 drinks 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.

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