The Overseas Highway to Key West is one of Florida’s most scenic road trips.
This 120-mile drive from Miami to Key West takes you through the Florida Keys, with turquoise waters, iconic bridges, beautiful beaches, and unforgettable stops along the way.
In this guide, you’ll find the best stops, things to do, and tips for planning your Florida Keys road trip.
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Driving the Overseas Highway: America’s Most Scenic Road Trip
We’ve crisscrossed a good deal of this country. I like to brag that our Ford Focus sedan, which I refer to as our “little tank,” has taken us all the way from Vancouver to Key West.
Having traversed much of the union, from the stunning vistas enjoyed in the Canadian Rockies, through the fog-covered forests of the Pacific Northwest, across the sun-scotched deserts of Nevada and Arizona, and down into the wet hot swamps of Louisiana and Mississippi, the beautiful backroads and highways have shown us the most memorable landscapes America has to offer.
And with that being said, the Overseas Highway stands a particularly exceptional experience.
Please don’t take our word for it. Go and see for yourself.
Why the Drive to Key West Is Worth It
Yes, you can fly into Key West. But please don’t.
The Overseas Highway is unlike any other road in the world. Dozens of bridges connecting dozens of islands stretch over 100 miles from the Florida mainland to the southern tropics.
The roadway divides the Atlantic Ocean from the Gulf of Mexico, though everywhere you look is the same magnificent hues of blues and greens.
The island towns along the way are the most authentic you’ve ever seen.
The gentle yet giant waters you’ll find yourself gliding will leave with a feeling of adrenaline and euphoria never thought possible in an SUV or minivan.
Even those who may fear bridges will find their phobias stifled by the sheer beauty of the views you are gazing upon.
Best Stops on the Overseas Highway from Miami to Key West
1. Key Largo: The Start of the Florida Keys Adventure
Those hoping to scuba and snorkel may want to pull off at the first major island, Key Largo.
The first underwater park in the country, John Pennekamp Coral Reef State Park is one of the best diving and swimming spots in all of Florida.
Amateur as well as professional photographers hoping to go sub-marine will find this one of the most picturesque places below (and above) the surface.
2. Islamorada: The Sportfishing Capital of the World
If you’re here to fish, then drive no further. (Just kidding. You must do at least a day-trip to the southern tip.)
But if the thought of landing a big fish far out in the Gulf Stream is your life’s (or weekend’s) wish, Islamorada is the Key to go to.
Various fishing charters offer a wide array of packages, from deep-sea day trips to afternoon jaunts just offshore.
A mecca for lovers of the “salt life,” it is flush with fine hotels and fresh seafood restaurants.
3. Marathon: The Heart of the Florida Keys
Smack-dab in the middle of the Keys is Marathon.
Those spending a solid chunk of time in the Florida Keys may find this the most ideal location.
One of the biggest and most developed of the Keys, various attractions from the Turtle Hospital to Sombrero Beach are just a few of the many family-friendly activities that can be found on Marathon.
4. Bahia Honda State Park: One of Florida’s Best Beaches
Known for crystal clear waters and fun little beaches, Bahia Honda State Park is a great place for a quick swim break.
The park also offers the best views of the old Overseas Railroad bridge, the precursor to the highway.
Abandoned in 1935 after a devastating hurricane, some remains of the rail line are still standing above the shores of Bahia Honda.
5. Big Pine Key: The Quiet Side of the Keys
Those hoping to enjoy a quieter slice of the island life may find Big Pine Key to their liking.
Known for calm waters and lush mangrove forests, the waters here are ideal for kayaking and wildlife viewing.
The famous Key deer are also prolific on this island, and it is advised to drive extra careful in order to both enjoy and avoid the majestic mammal.
What to Do in Key West
Watch the Sunset at Mallory Square
Right where the downtown meets the water (though all of Key West feels like one big downtown) is Mallory Square.
A wide open forum flush with magnificent ocean views and local street performers, the festive vibe is classic Key West.
The Key West Aquarium is also situated right next to the square, and offers an afternoon escape from the tropical heat.
2. Walk Historic Duval Street
Of all the tourist blocks in the world, Duval Street is up there among the most shameless. And I mean that in the best possible way.
My father called this road the “Duval Crawl” back in his fishing days.
Bars, t-shirt shops, and seafood establishments of all levels line the old avenues of Key West’s main drag.
Sloppy Joe’s is a particularly praiseworthy experience for any avid writer or lover of literature, as it was Hemingway’s favorite joint.
3. Visit the Ernest Hemingway Home
Never do I miss a chance to see the Hemingway Home.
Fans of the author, or of six-toed cats, will surely love strolling the grounds of the beautiful 19th century villa located in the heart of Key West.
His residence for many years, a museum to the writer can also be enjoyed inside the premises, just a stone’s throw from the main restaurants and shops.
Those hoping to be “in and out” can easily see the whole compound in 1 short hour.
4. Relax at Fort Zachary Taylor State Park
At the very tip of Key West is perched Fort Zachary Taylor State Park.
Clear waters make for excellent snorkeling, while lush nature trails make for excellent walks through the grounds of this historic Civil War fort.
One of the few beaches in this part of the Florida Keys, it is an ideal area for picnics and sunsets, though be forewarned it is small and can get quite crowded.
Whether a swimmer, hiker, or avid history buff, Fort Zachary Taylor State Park is an excellent way to cap off your day before hitting Duval Street for some nighttime food (and fun).
Best Time to Drive the Overseas Highway
As always with South Florida, the best time to be here is really December through March.
Cool and dry with no risk of hurricanes, the Sunshine State really earns its fame during these pleasant winter months.
With that being said, it is the busiest time of year here, and late spring also offers a good mix of nice weather and sparse crowds.
Whatever time of year you’re here, don’t skip this trip, and don’t leave later than sunrise.
Even if you don’t catch the daybreak over the Atlantic, the soft glowing colors of purple and orange across the islands and oceans is one of the most beautiful sights you will ever see.
Miami to Key West can take as little as 4 hours, so be kind to yourself and allow 2 extra hours for stops and meals.
It’s the journey, and the stops along the way… and the destination.
Truly every part is equally appealing and magnificent.
How Long Does It Take to Drive to Key West?
Miami to Key West can take as little as 4 hours, so be kind to yourself and allow 2 extra hours for stops and meals.
Once on the Overseas Highway, it is about 125 miles from the mainland to Key West. Those who drive nonstop can make it in 2 hours.
Beware of speed traps coming off the bridges and onto the islands… the troopers will get ya.
Coming back at sunset is equally beautiful, and often extra busy. Plan accordingly, and plan on stopping for grouper and oysters somewhere in Marathon or Islamorada.
Soak in as much of the Florida Keys as you can.
There is no place else like it in the world.
Final Thoughts: Take the Slow Road to Key West
The sun rises in the east and sets in Key West, if you plan your Overseas Highway trip accordingly.
As mentioned in other articles, Key West is a top 3 destination for me; I adore the town.
The journey there is one of the most breathtaking in the world.
The fish and cocktails are some of the most refreshing you will ever indulge in.
The accommodations have as much character as the bars and workers who fill them.
The nights are as clear as the ocean. The stars shine brighter, and the seabirds sing louder.
Even if Florida is not on your radar, Key West must be.
It is one of the top-tier destinations in the lower 48, and beyond.