Let America’s Southernmost Point Drive You Wild: Your Florida Keys Road Trip Itinerary

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Feel the salt spray as you drive from Miami to the eclectic Key West with this Florida Keys road trip itinerary.

Cover image on how to drive the Florida Keys

Why Drive the Florida Keys?

There’s a lot to do in the Florida Keys.

You can delve into world-class snorkelling spots, stuff yourself silly with seafood, or simply indulge in the laid-back island lifestyle. After years spent exploring this part of the United States, let me introduce you to this fun Florida Keys road trip itinerary.

How to drive the Floriday Keys

Just because America is in love with the automobile, doesn’t mean you need to be. Yes, you can hire your own car and have a blast. But if there’s a group of you, another good option involves chartering a bus from a company like BCS Bus Charter Then you can relax and enjoy the cocktails, while someone else deals with the parking and speed limits.

It makes sense to start in Miami (you can fly from London to Miami International Airport) but you can also fly into Orlando and take the new train to Miami, or pick up your vehicle in Orlando.

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How to Spend Seven Days Driving the Florida Keys

Day One: First Stop Miami

One look at Miami’s South Beach lets me know how cool the place is. One look in the mirror lets me know how cool I’m not.

“Hot water, clean sheets and stiff drinks,” promises the barman at the Whitelaw Hotel, as he slices watermelon and peach for the frosted cocktail glasses. In South Beach, the people are beautiful, the air is warm and a smoky lilac sunset accompanies clinking cutlery, rumbling jazz and cheek to cheek air kisses. Pastel pink Cadillacs glide past art deco buildings and I feel myself relax.

South Beach marks the breathing spot after the four hour drive from Orlando. It’s a chance to freshen up, feel the sand beneath your feet and get ready to head into nature’s own theme park: the Florida Keys.

These 45 islands, linked by the Overseas Highway, promise one of America’s greatest drives, laced with Caribbean sunshine.

And I’m ready to hit the road.

LeaVing Key Largo sign in the Florida Keys, USA

Day Two: Snorkelling in Key Largo & the Stone Crab Contest

One of the first things you’ll notice about a trip to the US is the attention to detail, particularly when it comes to people not being sued.

At the edges of the John Pennekamp Coral Reef State Park, my signature graces more pages for my snorkelling tour than it did for my mortgage application back home. A swimming and snorkelling lesson later, a step by step guide to lifejacket application followed by a tour of the boat’s safety apparatus and we’re finally ready to zoom off through the mangroves.

I look out for Flipper (he isn’t there,) crocodiles (nor are they) and finally my eyes rest on what we’ve come to see: a vast clump of coral, home to thousands of tropical fish. Purple stranded seaweed and luminous yellow cauliflowers bring the underwater world to life, making those reams and reams of paperwork more than worthwhile.

Back on dry land, we tuck into coconut shrimp and conch fritters at the Key Fisheries Market & Marina in Marathon. Slurping on a giant cup of soda, the poster for a stone crab eating contest catches my eye:

  • The first to finish 25 claws will win
  • 30 second deduction for each claw not picked and cleaned
  • Safety glasses will be provided and must be worn
  • Must crack your own claws
  • Over 18s only

To my disappointment, the contest isn’t for weeks. To get a glimpse of the wackier side of the Keys a bit sooner than that we need to keep on driving to reach the furthest Key in the chain: the wild west that is Key West.

Traffic on duval street in Key West, Florida

Days Three & Four: Key West

“We think of it as almost another country down there,” says my friend Margo, when I mention where I’m going.

At first glance, I’m not sure what she means.

Sure, the palm trees and conch shells make Key West look a little different. And there is that landmark that reminds you you’re only 90 miles from Cuba. But the America of the movies is also in rich supply: picket fences and mailboxes, brunch with blueberry pancakes and canary-yellow schoolbuses roaming through the streets.

Brunch at Blue Heaven gives me a clearer idea of what Margo had in mind. While sipping a milkshake, something fluttered at my ankles. Delusions of a jet-lagged mind, I thought at first, until it happened again, came with a brief pause and then crescendoed into a lung-curdling, alarm-clock beating cock-a-doodle-dooooooooooo!

There, at my feet, was a bona fide rooster, clucking and strutting around like it owned the place.

The kids loved it. And, after the initial shock, so did I.

Such quirkiness feels right at home in Key West. Men wear make-up and read from tarot cards, teens juggle with fire and old men stand on tightropes as the sunset flames across the sky. Each night in Mallory Square, the performances are different but the spirit remains the same.

Conch Shells and Lime

A low, throaty sound reverberates through the air as a man breathes into a salmon-pink conch shell. His name is Chuck and he invites me to have a go.

The technique sounds simple. The execution, as ever, brings problems.

The shell is the size of a cannonball, rippled with toffee-coloured stripes. You need to take a deep breath, clasp it with both hands and blow the loudest, soggiest raspberry you can muster right into the curled and crispy mollusc.

I think you can imagine the results – but perhaps I need to fill in the gaps. Picture, if you will, a dribbling disgrace of a raspberry, a whoopee cushion in front of the cool kids instead of a saxophonist set free.

I wash away the embarrassment with a lime soda cocktail and a slice of Key Lime Pie.

Lime, let me tell you, is a big deal in the Keys. Lime in pies, lime in drinks, lime in jams (sorry, jello) and everything in between.

Kermit’s Key West Key Lime Shoppe stocks them all: lime pepper, lime soap and the lime dish that started it all, the Key Lime Pie.

Hemingway and Butterflies

You’ll also find lime in the Cuban bars and restaurants offering a night out in Key West. Former haunts of Ernest Hemingway (whose colonial style villa today houses a museum) now entertain a Bohemian group of rock stars and vagabonds, a snapshot of those mainstream America left far behind.

Away from the parties, Key West still welcomes families, as the Key West Butterfly and Nature Conservatory makes clear.

The only thing you can’t do here is get away from it all. For that, you need to hop in the car, head back up the Keys and enter that chunk of America known as the backcountry.

Still debating about where to go? Here’s how to decide between Miami and Key West.

Bahia Honda State Park, florida keys road trip itinerary

Day Five: Kayaking in the Backcountry & Lazing on the Beach

Bill Keogh throws us a Kevin Costner smile and launches our kayaks into the water.

“I just love to get out among nature,” he says in a straight-from-the-movies drawl.

“Out there among the mangroves with the great big sky above,” he goes on, “you ain’t got nothing to worry about ‘cept what you wanna do next.”

I dip in a paddle and head for the mangroves, knowing exactly where I want to go next.

Bahia Honda State Park has won bucket loads of awards, including one for “Florida’s Best beach.” The sand is white, the water clear, and the vegetation suitably tropical. You can even pick up choc ‘n’ cherry cookies at the Sugar Loaf Food Company en route.

Dolphins on a Florida Keys road trip itinerary

Day Six: Trained Dolphins & Wild Birds

The Dolphin Research Center in Grassy Key allows you to ponder the significance of those Hitchhiker’s Guide to the Galaxy quotes, while swimming or painting with the dolphins, provided you book in advance.

Yet these are no ordinary dolphins. They hail from a pedigree that includes Flipper him or herself (the stunt dolphin, apparently, was a girl called Mitzi) and they come complete with a team of professionals who whoop, holler and howl their support from the sidelines, armed with buckets and buckets of fish.

Here, mankind has learned that dolphins can count, imitate one another and even teach men to pick up their socks from the bathroom floor. No wait, sorry, that last one was just a dream I had…

Back to reality in the Laura Quinn Wild Bird Sanctuary, we watch non-famous birds in silence.

Pelicans nuzzle against one another, while egrets, ospreys and saucer-eyed owls wait behind lattices of protective wire. All have been rescued and are too injured to return to the wild – a situation that repeats with the pilot whales we find the following day.

Boardwalk towards cocoa beach in the Florida Keys, USA

Day Seven: Saving the Whales, Cocoa Beach & Heading Home

Six volunteers from the Marine Mammal Conservancy Group hold the baby whale at the surface while their team leader fills a syringe for her nebuliser.

“Captivity is an ugly word,” he says, when I ask when the whales will be set free. “But sometimes these animals are too sick to survive on their own. I’ll never send them to a theme park, though. They were born to travel across water.”

I remember his words as we speed along the Overseas Highway towards Cocoa Beach.

Puffed clouds and blue water stretch away on either side and it’s obvious that whales aren’t the only ones born to travel across water.

People are too, at least in the Florida Keys.

Check out our Florida west coast road trip itinerary to extend your trip and don’t miss the Everglades National Park.

Making the Most of Your Florida Keys Road Trip Itinerary

Have Fun Outdoors

A big part of visiting the Florida Keys is having the opportunity to get outdoors and there’s so much more than just the marine life and beautiful beaches. While there’s plenty of fun to be had by donning a pair of walking boots and heading out on your own, there are other options too.

Big Pine Kayak Adventures specialise in Lower Florida Keys backcountry adventures including: half and full day kayaking nature tours, shallow-water skiff eco-tours  and sailing catamaran cruises.  It’s one of the best things to do in the Middle Keys.

Where: Big Pine Kayak Adventure, 1791 Bogie Drive, Big Pine Key, FL 33034

Market stalls in Mallory Square Florida

Fit in with the Locals

If you’re anything like me, fitting in with the effortlessly-cool Keys locals doesn’t exactly come easily. Don’t despair just yet though, there are some things you can do to avoid that terrible ‘tourist’ label…

  • Say “conch” with a hard “ch” so that it sounds more like “conk”
  • Go beyond the typical tick-list and try helping pilot whales with the Marine Mammal Conservancy Group
  • Chill out at sunset in Mallory Square, Key West to the sound of live music.
  • Avoid the peak season, especially spring break. The best time to follow this Florida Keys itinerary is between November and February. You can really appreciate the mangrove swamps, island chains and national parks while missing the worst of hurricane season.

Florida Keys Highlights at a Glance

  • Dry Tortugas National Park
  • Biscayne National Park
  • The Ernest Hemingway Home
  • John Pennekamp State Park
  • Street performers
  • White sandy beaches
  • Florida Keys Wild Bird Center
  • Seven Mile Bridge
Food platter in a Miami restaurant
Florida takes food seriously

Eat Well

The food in the Florida Keys is no joke. Don’t miss:

  • Keys Fisheries – a great spot for coconut shrimp and a good time
  • Meson de Pepe – for a taste of Cuba after you’ve grabbed your photo of the mile marker at the southernmost point
  • Blue Heaven – on of the best places for blueberry pancakes & roosters

What to Pack

There are a few specific items that you should remember to pack to help make the most of your time in the Florida Keys.

  • Long sleeved cotton tops, insect repellent and tiger balm to fight off the mozzies.
  • Plenty of sunscreen – you’re in the sunshine state!
  • Your camera – sunsets here are among the best in the world.

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