FloridaMiami to Key West: Best Places to Stop Along the Drive
Day Trip to Islamorada Florida Keys

Miami to Key West: Best Places to Stop Along the Drive

Driving from Miami to Key West is like flipping through a postcard book of paradise. It’s jaw-dropping coastal views, quirky roadside attractions, and enough seafood shacks to keep you happily sated with conch fritters and key lime pie. This drive along the Overseas Highway is more than a journey; it’s an experience. SYou could rush through in an afternoon, but why would you? Take it slow, spread it out over three days, and let the magic of the Keys sink in.

Miami to Key West Drive: Top Attractions Along the Way

Imagine this: the sparkling Atlantic Ocean to your left, the shimmering Gulf of Mexico to your right, and a ribbon of asphalt that skips across 42 bridges, linking 44 islands. Manatee-shaped and flamingo-shaped mailboxes dotting the landscape. And the views? Simply distracting.

Florida Keys: A Road Rich in History

Picture this: The string of coral islands that arc from the Florida peninsula south toward Havana has always been a magnet for pirates, profiteers, and anyone craving that Caribbean vibe right within the U.S. Henry Flagler, an ambitious developer, had a vision to turn these islands into a tropical playground for the rich and famous in the early 20th century. He extended his railway all the way from Miami to Key West, making it accessible to tourists. Today, that railway has been transformed into the Overseas Highway—a must-do journey for any traveler.

Must-Visit Places on Your Road Trip from Miami to Key West

Upper Keys

Key Largo

The adventure kicks off in Key Largo, just over an hour’s drive from Miami International Airport. Here, the suburban sprawl gives way to Everglades bogs and lush, tropical scenery. First stop: Dagny Johnson Key Largo Hammock Botanical State Park. Stretch your legs, breathe in the fresh air, and join bird-watchers who can identify a palm warbler by its call.Known as the “Diving Capital of the World,” it’s a haven for underwater adventurers. Stop by John Pennekamp Coral Reef State Park for snorkeling or a glass-bottom boat tour.

Hungry? Hit up the Fish House restaurant, festooned with tiki and flamingo lights—it’s a local favorite. And if you love the ocean, you’re in luck. Key Largo is a diver’s dream, with John Pennekamp Coral Reef State Park offering snorkeling tours over vibrant corals and tropical fish in protected waters.


Islamorada: Where Art and Fishing Collide

Drive south, and you’ll hit Islamorada – a 20-mile stretch of tropical charm spread across six islands. This community boasts old-money heritage and is hailed as the sport fishing capital of the Keys. Even former President George H.W. Bush couldn’t resist its allure; he ran a bonefishing tournament here for a decade.

But there’s more. Remember the Netflix series “Bloodline”? Yup, it was filmed here. The fictional Rayburn House from the series is actually the Blue Charlotte villa at the Moorings Village. With 18 rental cottages dating back to the mid-1930s, the place oozes character.

Feeling peckish again? Head to the Morada Bay Beach Cafe or Pierre’s for a sunset dining experience you won’t forget. The eclectic mix of roadside inns, artsy cafes, breweries, and galleries gives Islamorada a bohemian flair. Don’t miss the self-guided tour via the Florida Keys History & Discovery Center app for a dive into local history, including hurricanes, pirates, and island pioneers.

Indian Key

Feeling adventurous? Time to go waterborne. From Islamorada, head to Robbie’s Marina and take a boat to Indian Key Historic State Park. This mangrove-fringed island was once a bustling wrecking village in the 1830s, salvaging goods from shipwrecks. Walk through the shady trails lined with tamarind and sisal plants, and let your imagination take you back in time to when this island was the seat of Dade County.

Middle Keys


Halfway down the Keys lies Marathon, a family-friendly spot with plenty of activities. Fancy a stroll? Check out the Seven Mile Bridge—it’s a must-see. For marine life enthusiasts, the Turtle Hospital offers tours where you can meet recovering sea turtles.


Drive another 30 miles south, and you’ll find yourself in Marathon. This is where commerce meets conservation. Lobster traps line the streets, and Keys Fisheries offers an authentic taste of the local catch—order a lobster Reuben under a superhero pseudonym for some quirky fun.

Marathon is also home to the Dolphin Research Center and the Turtle Hospital. These nonprofit marine attractions fund their operations largely through visitor tours. At the Turtle Hospital, you’ll see everything from an operating room to tanks filled with turtles recovering from various ailments. It’s a touching reminder of the delicate balance between nature and human activity.

Bahia Honda State Park

A little further down, Bahia Honda State Park boasts some of the best beaches in the Keys. Take a dip, go snorkeling, or just relax on the sandy shores. This is the perfect spot to soak up some sun and unwind.

Lower Keys

Big Pine Key

Welcome to the Lower Keys, where things get even more secluded and serene. Big Pine Key is your stop if you’re a nature lover. This island is home to the National Key Deer Refuge, where you can spot the adorable and endangered Key deer. Keep your camera ready; these little guys are Instagram gold.

Bahia Honda State Park

Another gem in the Lower Keys is Bahia Honda State Park. This park boasts some of the best beaches in the Keys, with clear waters perfect for snorkeling and swimming. The old Bahia Honda Rail Bridge adds a touch of historical charm to your visit.

Stock Island: The Up-and-Comer

As you cross into Stock Island, you’ll notice it retains a touch of grit and authenticity. Once a blue-collar haven for shrimpers and fishermen, it’s now a mix of old and new. Head to the Perry Hotel Key West for a taste of luxury. Their main restaurant, Matt’s Stock Island Kitchen & Bar, serves upscale versions of local seafood that’ll make your taste buds dance.

Key West

Finally, we arrive at the crown jewel: Key West. This place is everything you’ve heard and more. It’s quirky, vibrant, and full of life. From the historic Hemingway House to the lively Duval Street, Key West is where the journey culminates in an explosion of fun and culture.


Driving from Miami to Key West is where you embrace the slow lane, soak in the salty air, and let the rhythm of the islands guide you. Whether you’re diving in Key Largo, fishing in Islamorada, or roaming the quirky streets of Key West, this journey is one you won’t forget.

I believe that you can travel the world without quitting your job. I believe that you can experience all the magic, the foodies and the cultures of the world while having a normal life. And, perhaps, two dogs. This is exactly what I’ve been doing for 15 years. This is exactly what my blog is about. Love, Lilia

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