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Writer's pictureDianna Janas

Miami to Key West: The Ultimate Road Trip Through Paradise



Ah, the open road! There’s something irresistible about a road trip, especially when it’s not just any road but the iconic Overseas Highway, connecting Miami to Key West. Imagine driving straight into a postcard, with turquoise waters on both sides and endless possibilities for fun, food, and fantastic memories. So, buckle up—this isn’t just a road trip; it’s a journey to the heart of the Florida Keys, where life slows down, and the sunsets are so stunning they deserve a standing ovation.



Pit Stop 1: Key Largo – First Key, First Wow

Start your adventure with a bang—or rather, a splash—at Key Largo, the self-proclaimed "Diving Capital of the World." Whether you’re into snorkelling, scuba diving, or just dipping your toes in the ocean, John Pennekamp Coral Reef State Park is your spot. Don’t worry if you’re not a diver; the park’s glass-bottom boat tours let you peek into the underwater wonderland without getting wet.

Before you leave, grab a key lime pie (your first of many, trust me) from a roadside stand. You’ll need to fuel up—for science, of course.


Pit Stop 2: Islamorada – Sport Fishing & Stories

Welcome to the "Sport Fishing Capital of the World!" Islamorada is where Hemingway wannabes and fishing enthusiasts converge. Not into fishing? No problem. Swing by Robbie’s Marina, where you can hand-feed the tarpon. Picture it: you, a bucket of fish, and these hungry, leaping giants. It’s half thrill ride, half nature documentary, and fully unforgettable.

Pro tip: Before you leave Islamorada, make sure to grab a rum cocktail at Lorelei Restaurant & Cabana Bar. Watching the sunset here feels like a little slice of heaven.


Pit Stop 3: Marathon – Bridges and Beaches

Ah, Marathon. This is where you’ll cross the famous Seven Mile Bridge—a feat of engineering that’s so long it feels like you’re driving into the horizon. Before hitting the bridge, stop by Sombrero Beach for a quick swim or visit the Turtle Hospital to learn about the incredible work done to rehabilitate sea turtles. Spoiler alert: You might leave wanting to adopt one.


Pit Stop 4: Big Pine Key – Wild and Wonderful

Slow down as you approach Big Pine Key—literally. This area is home to the adorable (and tiny) Key deer, and they have the right of way. Take a detour to Bahia Honda State Park, where the beaches are so pristine they look Photoshopped. This is the kind of place where you sit in the sand, stare at the ocean, and think, Why don’t I live here?




Final Destination: Key West – The End of the Road

Cue the applause—you’ve made it to Key West! This quirky, colourful island is like no other. Start your visit at the Southernmost Point Buoy for the obligatory photo op, then wander down Duval Street, where you’ll find everything from art galleries to bars with live music.

History buffs can explore the Ernest Hemingway Home & Museum, home to the writer and his six-toed cats. Adventure seekers should book a sunset sail or rent a bike to explore the island’s hidden gems.

End your day at Mallory Square for the nightly Sunset Celebration. Street performers, food vendors, and that glowing golden orb dipping into the sea—what better way to toast to the end of your road trip?



Don’t Leave Without This!

For a truly stress-free adventure, make sure you’ve got a GPS-enabled tour guide app—perfect for keeping you on track and sharing fascinating stories about the Keys as you go. Available through your travel agent (me!), it’s your co-pilot for the ultimate road trip.

Tips for the Journey

  • Playlist: Curate a road trip playlist featuring Jimmy Buffett, Bob Marley, and maybe a little Harry Belafonte for good measure.

  • Snacks: Stock up on fresh fruit, salty snacks, and (obviously) key lime treats.

  • Wardrobe: Flip-flops, sunscreen, and breezy outfits are your best friends.

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