Road trip through the Florida Keys

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Rather than flying to Key West, we rented a car at the Miami airport and drove from Key Largo to the “Last Resort” on U.S. Route 1, one of the longest over-water highways in the world. We loved every mile of the two-lane Overseas Highway.

Forty-two bridges link a string of tropical islands that head westward into the setting sun. In the early 20th century, train travel was the only way to get from Miami to Key West. In 1935, a Labor Day hurricane demolished the railroad and killed more than 400 people. This act of nature led to the building of the Overseas Highway.

Enjoy the beaches along the keys
Enjoy the beaches along the keys

Key Largo

Key Largo anchors the northeastern leg of our journey. Mile markers on the island run from mile marker 90 to mile marker 106. (You can’t get lost in the Florida Keys because there’s only one road in and out, and it has these little green signs that mark your miles.)

Though famous for “Bogie and Bacall” (the movie Key Largo, starring Humphrey Bogart and Lauren Bacall, was filmed in 1948), the island is also known for the John Pennekamp Coral Reef State Park, established in 1963 as the first underseas park in the United States. Visitors here can take a 2½ hour cruise on the glassbottom boat Spirit of Pennekamp.

The boat, 65 feet (20 m) in length, carries 130 passengers over park waters and the Florida Keys National Marine Sanctuary, 178 nautical square miles (611 km² ) of colorful coral reefs, seagrass beds and mangrove swamps. The park also offers snorkeling, fishing, swimming, camping and picnicking for those wanting to stay a while.

Large Sea Anemone living at the Florida Keys National Marine Sanctuary
Large Sea Anemone living at the Florida Keys National Marine Sanctuary

Crossing Bridges

We keep driving, though. And as we cross from the rustic fishing village of Tavernier onto Plantation Key, the majesty of our trip unfolds. This first major bridge along the way divides the glittering green waters of the Gulf of Mexico on our right from the Atlantic Ocean on our left. And below the surface of these 30-foot (9 m) depths sit nearly a dozen Spanish ships that sank during a hurricane in the 1700s.

From Plantation Key, we cross a bridge onto Windley Key, the highest elevation in the Florida Keys, at 18 feet (5.5 m) above sea level. Two miles (3.2 km) and another bridge later, we enter Upper Matecumbe Key and Islamorada, the self-proclaimed sportfishing capital of the world.

We’re hungry. Time to stop for a late lunch at the Islamorada Fish Company, where a tanned waiter serves us fresh grouper, conch fritters and cold beer on a dockside table near shrimp boats and envious pelicans. Conch fritters and key lime pie are required eating on this island chain. We grab some free recipes and a to-go cooler of the house specialty, in-season stone crab claws that we will savor during a Key West dinner.

After the meal, we change into shorts and T-shirts. Because it’s still winter in the Florida Keys, we are blessed with bright, sunny skies, daily highs in the 70s (around 21 C) and little, if any, rain.

Summers can be challenging, though, with mosquitoes and hurricanes driving many of the locals northward between June and September. But the area comes alive again in October when the eight-month season is greeted by a Fantasy Fest celebration in Key West.

There’s only one road out on this Florida Keys island-hopping adventure, but it’s likely the laid-back atmosphere will make you want to stay.

Heart of the Keys

We point the car southwest and cross six bridges in a 10-mile (16 km) stretch that leads us onto Long Key, the unofficial beginning of the Middle Keys area. Long Key State Park is a favorite among divers, campers and fishermen, who enjoy the nature trails and ancient coral reefs in the Florida Keys.

Three more bridges connect several small keys in the 18-mile (29 km) drive to the Vaca Cut Bridge into Marathon, the half-way point of our journey. Along the way, we watch kayakers and sailboaters play in the shallow, clear waters near the shores of Duck Key, Grassy Key and Crawl Key.

Known as the “Heart of the Keys,” Marathon is the busiest area on our jaunt. Gas stations, souvenir shops and fast food joints line the highway on both sides. Small chartered planes approach Marathon Airport, the only commercial landing strip between Miami and Key West.

But the highlight of the area (and the entire trip) is the famous Seven Mile Bridge, which runs from mile marker 47 to mile marker 40 after we leave Marathon. There are places on the bridge where we see nothing but sky and water… like we’re riding with E. T. on a bike into another dimension, or sailing on a cruise ship. That changes-in-attitude feeling is kicking in, and we let it take over.

Seven Mile Bridge in the Florida Keys
Seven Mile Bridge in the Florida Keys

On our right runs the old, narrow bridge, now used by fishermen, bus-driven tourists and joggers headed to Pigeon Key, a 5-acre (2 hectare) island located two miles (3.2 km) out from the Marathon side. Pigeon Key served as home base to Henry Flagler’s construction workers when they built the overseas railroad from 1906 to 1912, and a museum there memorializes their efforts.

This old bridge was also a setting in the movie True Lies (1994), in which Jamie Lee Curtis was pulled by Arnold Schwarzenegger through a limo roof to the safety of a helicopter before her driverless car plunged into the ocean. We can see a gap in the bridge where the scene was filmed.

Gap in bridge at Bahia Honda State Park
Gap in bridge at Pigeon Key

Lower Keys

We leave our surreal crossing and touch down on Little Duck Key to start the last third of our journey through the Lower Keys.

Three bridges later we arrive on Bahia Honda Key, site of scenic Bahia Honda State Park, known for its beautiful beaches and excellent snorkeling. The Sand and Sea Nature Center offers a sea-life display, a small marine aquarium and a ranger program with beach walks, talks and other activities regularly scheduled.

Five miles (8 km) and two bridges later we are on Big Pine Key, home of the Key Deer Refuge. Blinking speed-limit signs caution us to drive slowly; some of the dog-sized deer that live on this island wander onto the busy highway at the wrong time. Big Pine is also home to many of the housecleaners, groundskeepers and restaurant workers who tend to the wealthy locals of Key West.


We stop for a cold drink at Mangrove Mama’s, an outdoor seafood eatery on Sugarloaf Key. A long-time Sugarloaf resident at the next table says, “I make the 15-mile drive into Key West nearly every day to work out or eat out. And I never get tired of the view or the drive.”

We understand why. Most of the bridges along our way are in the Lower Keys, and we cross 21 of them in a 26-mile (42 km) stretch south of Big Pine. Down the road from Mangrove Mama’s, a small plane takes off from Sugarloaf Airport to drop skydivers into puffy clouds. Just past Sugarloaf, we pass over an uninhabited group of islets called the Saddlebunch Keys.

Ocean views at Bahia Honda State Park

Key West

The U. S. Naval Air Station on our left, at Boca Chica, is the last busy area before we cross a final bridge from Stock Island into Key West. The Air Station was commissioned in 1917 when the Navy discovered that this location offered the most days of perfect flying weather in the country. Noisy jets in the skies above testify that the place is still active.

We arrive on the southernmost island of Key West a short time before sunset to 8 square miles (21 km²) of frolicking, free-spirited fun, in the mood for the “Conch Republic.” The so-called micronation was born after a tongue-in-cheek protest secession of the city of Key West from the United States on April 23, 1982, and it has been a tourism booster for the city ever since.

No longer the neophytes that drove through Key Largo four hours earlier, we have changed from tense, cold-country folks into laid-back, ex-officio subjects of the Conch Republic.

Sunset in the Florida Keys
Sunset in the Florida Keys

Book This Trip

See our Florida Travel Guide for more on what to see and do on your trip!

Start planning your road trip vacation through the Florida Keys today! Find flights and rental cars at the best comparable rates here through Kiwi. When you’re ready to travel, find hotel or VRBO options, popular local restaurants, insider tips on how to get around and more through Travelocity and TripAdvisor.

If you are looking to learn more about the keys or enjoy some island fun, check out GetYourGuide. Book tours, ocean activities and skip-the-line tickets all over the Florida Keys here.

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