Florida Keys Overseas Highway: Cross 37 Iconic Bridges

The Florida Keys Overseas Highway is more than just a scenic drive—it's a journey steeped in history, engineering marvels, and unparalleled natural beauty. Stretching 113 miles from Key Largo to Key West, this highway is one of the most famous roadways in the world.

Built along the path of the historic Florida Keys Over-Sea Railroad, which first opened in 1912, the Overseas Highway transformed the way people experience the Florida Keys. Today, this All-American Road is a symbol of freedom and adventure, earning its place as one of the top 10 greatest drives in the U.S.

The highway is a feat of modern engineering, connecting 42 islands via 37 bridges, including the famous Seven Mile Bridge, which was the longest bridge in the world when it opened in 1982. Driving this route, you’re not just crossing from point A to point B—you’re gliding through the open ocean, with breathtaking vistas at every turn.

According to recent statistics, the Florida Keys see over 5 million visitors each year, many of whom choose to drive the Overseas Highway to experience the thrill of being surrounded by nothing but turquoise waters and endless sky. The drive has even been listed in National Geographic’s top 500 drives of all time, making it a must-do for road trip enthusiasts.

Top Sights Along the Overseas Highway

Your journey along the Florida Keys Overseas Highway offers countless opportunities to explore and discover. Each island has its own distinct character, making the drive both exciting and diverse. Here are the top spots you won’t want to miss:

1. Key Largo – The first stop along the Overseas Highway, Key Largo is home to the Florida Keys National Marine Sanctuary and John Pennekamp Coral Reef State Park, the first undersea park in the United States. The park protects 70 nautical square miles of coral reefs, seagrass beds, and mangrove swamps, offering incredible snorkeling, scuba diving, and glass-bottom boat tours.
2. Islamorada – Known as the "Sport Fishing Capital of the World," Islamorada boasts world-class fishing charters and the famous Robbie’s Marina, where you can hand-feed giant tarpon. This village of islands is also home to the History of Diving Museum, giving visitors a fascinating look into underwater exploration.
3. Seven Mile Bridge – Spanning a remarkable seven miles over open water, the Seven Mile Bridge is the most iconic part of the Florida Keys Overseas Highway. This engineering marvel offers stunning 360-degree views of both the Atlantic Ocean and the Gulf of Mexico. Fun fact: The original bridge, built in 1912, still runs parallel to the modern bridge and is used as a fishing pier and walking path.
4. Marathon – Located in the Middle Keys, Marathon is the perfect place to stretch your legs and take in some of the region’s best wildlife experiences. Visit the Turtle Hospital, which rehabilitates injured sea turtles and educates visitors on conservation. Marathon is also known for its Sombrero Beach, a quiet spot perfect for a picnic or swim.
5. Key West – The final stop on your adventure, Key West is not just the southernmost point of the U.S., but a destination filled with charm, history, and vibrant culture. As you arrive, you’ll pass the famous Mile Marker 0, signifying the end of the Overseas Highway. Explore Ernest Hemingway’s home, visit the lively Mallory Square for the nightly sunset celebration, and unwind in one of Historic Key West Vacation Rentals' luxurious homes.

Insider Tips for a Seamless Journey

To get the most out of your trip down the Florida Keys Overseas Highway, here are some key tips from seasoned travelers:

• Time Your Trip Right: For the best weather and fewer crowds, plan your drive during the shoulder seasons (April to early June and September to November). During these times, temperatures range from the mid-70s to low 80s, ideal for outdoor activities.
• Pack Light but Smart: Make sure to bring plenty of sunscreen, a hat, and sunglasses. The sun reflecting off the water can be intense, and you'll want to stay comfortable as you explore the islands.
• Stop for Photos: With 42 islands and countless scenic overlooks, be sure to pull over safely to capture those Instagram-worthy moments. The Bahia Honda State Park offers some of the best views of the Seven Mile Bridge and is the perfect place for a pit stop.

Unwind in Key West with Historic Key West Vacation Rentals

After completing the Overseas Highway, your adventure doesn’t stop when you reach Key West. In fact, this vibrant island is where your vacation truly begins. Why settle for an ordinary hotel when you can stay in a historic, beautifully restored vacation home that lets you experience the unique charm of Old Town Key West?

Historic Key West Vacation Rentals offers a variety of accommodations, from charming cottages to luxurious Victorian mansions, each located just steps from iconic landmarks like Duval Street and the Southernmost Point. Staying with us allows you to experience Key West’s world-class dining, lively arts scene, and laid-back island vibe.

Imagine waking up in your own private home, just a short walk from the beach or your favorite café. Whether you’re staying for a few days or planning an extended trip, we have properties that will make you feel right at home.

Contact Historic Key West Vacation Rentals today to book your nightly, weekly or month-long stay in one of our fabulous properties in Key West. Here’s a small sampling of what awaits intrepid travelers, whether or not you opt to make that famous road trip from Miami:

• Butterfly Cottage: You can’t help but get into the local vibe from the front porch of this sweet completely removed home. With room for four, this 2 BR, 2 BA charming property is situated on a quiet lane just two blocks from bustling Duval Street, with its vibrant shops, galleries, bars and restaurants. A nightly rental, Butterfly Cottage offers an open concept living and kitchen space, with large glass doors opening up to a private back deck with a hot tub and outdoor shower. Both bedrooms feature ensuite bathrooms and gorgeous furnishings. Best of all, you can walk to Old Town Key West, or hop on the free Duval Loop shuttle bus.
• Fair Winds at the Foundry: Your home for the week begins by unlatching the white picket fence out front, where you’ll be delighted to find this 2 BR, 2.5 BA three-story townhouse flooded with natural light, vaulted ceilings and an open concept living area. Two bedrooms are located on the second and third stories, with a private balcony available to the master bedroom. Fair Winds at the Foundry is located in the exclusive and historic Truman Annex, which President Harry Truman claimed as his winter home. Dominated by palm trees and charming residences, Truman Annex is in the middle of all Old Town Key West has to offer. You’ll find yourself just steps away from the beach, as well as all the action on Duval Street.
• California Dreaming: You can’t help but find yourself living like a local with an extended Key West vacation stay in this gorgeous pink-shuttered 4 BR, 3 BA home for 7 people. Dominated by natural light, California Dreaming features deluxe appointments, like a wet bar with both filtered and carbonated water taps and many other high-end appliances. Go ahead and work from home in the large office, featuring two workstations. Later, you can cook up something special on the Italian Bertazzoni range in the chef’s kitchen, then dine alfresco out back in a lushly landscaped pool area. Venture out for the nightlife by walking to the White Street Pier and the southern end of Duval Street from this convenient Old Town location.

Explore our Key West vacation rental options and book your perfect stay today!

Start Your Journey Today

Ready to experience the Florida Keys Overseas Highway for yourself? Don’t miss out on one of the most unforgettable road trips in the world. From the breathtaking scenery to the vibrant culture of Key West, this adventure has it all. And when you’re ready to relax, Historic Key West Vacation Rentals is here to welcome you with luxurious accommodations that will make your trip even more memorable.

Contact us now to book your dream vacation and discover why a road trip down the Florida Keys Overseas Highway is the ultimate escape to paradise!