America's Most Famous Drives: Overseas Highway

Long Bridge at Florida Keys Historic Overseas Highway
Long Bridge at Florida Key's Historic Overseas Highway | © Simon Dannhauer / Alamy Stock Photo
Alexia Wulff

The Overseas Highway, Florida’s old railroad-turned-highway, connects Miami to Key West. There’s loads of attractions, places to stay and spots to eat along the way – all included in this epic road trip guide.

Crossing coral and limestone islets along its 113mi (181km) path, the Overseas Highway is considered one of the most fascinating scenic routes in all of the US. For how to make the most of this drive, read our guide to Florida’s Overseas Highway.


Sometimes called the Highway that Goes to Sea, the Overseas Highway is a modern marvel that allows drivers to travel over South Florida waters to the highly regarded Key West, leapfrogging from island to island to the southernmost city in the contiguous 48. Along the way, visitors can revel in historic shipwrecks, secluded islands, abundant wildlife and unforgettable seascapes under the cloud-flecked sky. After the Florida East Coast Railroad – constructed in 1912 – closed due to damage and economic problems in 1935, 42 giant steel and concrete bridges were added, completing 113mi (181km) of the Overseas Highway by 1938, an incredible engineering feat still to this day. Today, this All-American Road sees more than 3m visitors per year.

South Beach, Key West, Florida, USA

What to do & see

While many visitors typically head straight to Key West (an achievable drive in four hours), there are plenty of noteworthy stops along the way. Starting in the most northern Key, Key Largo, stop here for world-class diving, a shoreline dotted with natural and man-made reefs, historic shipwrecks and an underwater hotel, Jules’ Undersea Lodge. Here guests dive over 25ft (8m) down to their rooms after check-in. Next up, pop into Islamorada, a string of islands named the sport fishing capital of the world, for a tropical catch-of-the-day, or opt for a fishing charter off the coast of the islands. This is a must-stop for food lovers as it boasts an array of top-notch restaurants featuring local cuisine and world-renowned chefs.
In Marathon, get a behind-the-scenes look at the world’s first sea turtle hospital, or pet dolphins at the Dolphin Research Center – the perfect family-friendly pit stop. Just before reaching Big Key, 40 minutes outside Key West, don’t miss the Bahia Honda State Park where visitors can kayak, snorkel and sunbathe. Once in Big Key, a mangrove and pine-forest-lined town surrounded by a bed of coral reefs, spot nearly untouched flora and fauna. At the end of the road, head to the open-air Key West Aquarium, the Hemingway House & Museum, the historic Heritage House Museum, the Key West Lighthouse Museum, the Harry S. Truman Little White House, Nancy Forrester’s Secret Garden, Fort Zachary Taylor State Historic Site and Mel Fisher Maritime Museum. Don’t miss the Bahama Village, filled with Caribbean culture, the Historic Seaport, the Wrecker’s Museum and West Martello Tower – a stunning orchid and butterfly garden. Other activities include fishing, boating, sailing, sunbathing, snorkeling, diving and sunset watching.

Where to stay

Along the Overseas Highway, the lodging is plenty, though most hotels are on the pricier side, especially during high season. For stays in Marathon, head to the Hammocks at Marathon or the Holiday Inn Express & Suites Marathon for a budget-friendly stay. Opt for the Tranquility Bay Beach House Resort or Hyatt Place Marathon Florida Keys for a little extra. Other popular hotels include Parmer’s Resort in Little Torch Key, Glunz Ocean Beach Hotel & Resort in Key Colony Beach, Hawks Cay Resort in Duck Key, Sugarloaf Lodge in Sugarloaf Key, BayView Inn Motel and Marina in Conch Key and Lime Tree Bay Resort in Long Key. Once in Key West, book a budget-friendly stay at the Grand or Nancy’s Guest House, or opt for a more luxurious stay at the Southernmost Beach Resort, situated on the shores of the water.

Along the Overseas Highway, the lodging is plenty

Where to eat & drink

For local cuisine – stone crab, key lime pie, lobster and conch fritters – heading straight to Key West is recommended. However, there are a few stops along the way, including Islamorada’s new Florida Keys Brewing Co. and Pierre’s, Harriette’s Restaurant and Hobo’s Cafe in Key Largo, Barracuda Grill and Florida Keys Steak and Lobster House in Marathon, the Dining Room in Little Torch Key and No Name Pub in Big Pine Key, an institution since 1931. Once in Key West, get your hands on local cuisine at Roof Top Café, the Stoned Crab, Blue Heaven, el Siboney Restaurant and Seven Fish.

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

Our immersive trips, led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

All our travel guides are curated by the Culture Trip team working in tandem with local experts. From unique experiences to essential tips on how to make the most of your future travels, we’ve got you covered.

Culture Trip Spring Sale

Save up to $1,656 on our unique small-group trips! Limited spots.

Edit article