7. Overseas Highway
To drive the Overseas Highway – the southernmost leg of US Route 1 – is to witness an engineering, natural and scenic marvel. Running from Miami to Key West, the 113-mile byway includes 42 overseas bridges, traversing through tropical savanna over the Florida Straits.

Entering Key Largo (Photo: J. Konrad via Flickr)
The road has an interesting history. It began as the Overseas Railroad, which was completed in 1912 and brought tourists and trade from the Florida mainland to the Keys en masse. When the railroad was heavily damaged during the Labor Day Hurricane of 1935, the railroad was unable to afford repairs, so they sold the remaining roadbeds and bridges to the state of Florida for $640,000.

Over the years, the highway has seen many additions, adjustments and improvements – most noticeably in the early 1980s, when most of the bridges along the route were replaced and widened.

In 2009, the Overseas Highway was named an All-American Road by the National Scenic Byways program – a prestigious title only 30 other roadways in the nation have earned. The drive straight through from Miami to Key West only takes four hours – but if possible, take your time, make frequent stops along the route, and if you can, stay overnight on some of the lesser-visited islands. They’re every bit as beautiful as Key West, and full of fun, quirky and picturesque attractions. Keep your eyes peeled for indigenous animals like the American crocodile and Key deer (North America's smallest species of deer), osprey, great white herons and roseate spoonbills. Enjoy the roadside recreational areas along this incredible roadway. And of course, make time to relax and enjoy at least one of the dramatic sunsets the Keys are known for.

Key Largo

Photo: Jules Undersea Lodge
Just 60 miles from downtown Miami lies Key Largo, a beloved destination for scuba divers. If diving is your thing, you must make a pit stop at Jules’ Undersea Lodge. Set in a scenic lagoon, scuba-certified visitors can spend the night in an underwater cottage that features hot showers, a kitchen (complete with refrigerator and microwave), books, music, and even movies. If sleeping underwater is too intimidating, you can indulge in a 3-hour pizza lunch excursion instead – then continue down the road to Islamorada.


Photo: Lorelei Restaurant, Marina & Cabana Bar
Just as Key Largo is known for diving, Islamorada is famous among the fishing set. As the Gulf Stream flows north, it brings a steady flow of game fish like sailfish, tuna and kingfish, along with their smaller cousins, tarpon, trout and mullet.

Fishermen aren’t the only ones taking advantage of this bounty. In recent years, Islamorada has become a blossoming foodie destination, with local chefs taking advantage of the scenery and fresh catches. A perfect place to enjoy a sunset meal is Lorelei Restaurant, Marina & Cabana Bar . Guests can arrive by boat, car or foot to enjoy the nightly Sunset Celebration, which features live music and a happy hour from 4–6 p.m. (If you’re passing through earlier in the day, they’re open for breakfast and lunch, too). Beer aficionados will enjoy Florida Keys Brewing Company - the first microbrewery on the Upper Keys - located in the Morada Way Arts & Cultural District.


Seven Mile Bridge (Photo: Dan H via Flickr)
Even if you’ve never driven the Overseas Highway, you’ve probably seen one of its most famous landmarks. Seven Mile Bridge connects the Middle Keys to the Lower Keys, and has been seen in movies such as True Lies, 2 Fast 2 Furious and Mission Impossible III. There are actually two bridges along this section of the byway - the newer section is for car traffic, while the old section is open strictly to cyclists and pedestrians (who can fish from the side).

A worthy stop along this section of the route is The Turtle Hospital, a nonprofit that rehabilitates injured sea turtles. The organization has successfully treated and released over 1500 Sea Turtles since its founding in 1986. Visitors can take a guided 90-minute tour of the facilities where they receive a behind-the-scenes look at rehab center, learn about conservation and feed the local residents.

Big Pine Key

Key Deer National Wildlife Refuge. (Photo: J. Paz via Flickr)
Named for the massive pine trees that grace its landscape, Big Pine Key is home to the largest population of the endangered Key deer. Visitors can visit the National Key Deer Refuge – home to 800 of the animals - where you can hike, fish, kayak, or simply take in the gorgeous scenery.

Robbie's Marina is a favorite stop. Relax atop the spacious deck with an icy cocktail, or feed the giant tarpon that hang out underneath. In addition to the restaurant, Robbie’s rents fishing and snorkeling equipment, and offers guided eco-tours and sunset cruises. There’s also a gift shop with wares and art from local artists. All in all, a fun way to spend a day!

No trip to Big Pine Key is complete without a stop by No Name Pub. A Big Pine institution since 1936, this pizza and seafood restaurant is a favorite of locals and tourists alike. Originally a general store that also sold bait and tackle, the building once housed a small brothel as well. Thousands of dollar bills cover the walls, and the vibe is quirky and fun. Whatever you do, don’t miss the homemade conch chowder.

Nine miles from Big Pine key is Little Torch Key, home of Boneafide Fishing Charters . The company offers several specialized options depending on what you want to fish for, including wreck and reef, sandbar, inshore and tarpon-focused excursions. Operated by a South Florida local who’s been fishing since he could walk, there’s nothing like learning all the best fishing spots from someone who knows them like the back of his hand.

Key West

You’ve made it to the end of the Oversea Highway, so let the good times roll. Key West is a magical place, with history, nightlife, wonderful, interesting people and fantastic eats.

Stroll the shops and galleries along Duval Street, visit the Ernest Hemingway Museum (located is his former home), or hop on the Conch Tour Train for a relaxed tour of the island. Come nightfall, enjoy the bustling nightlife and music scene the island is known for.

by Davina van Buren
Route Details
Key West
113 miles
4 hours
Recommended Stopovers
  • 1. Key Largo
  • 2. Islamorada
  • 3. Marathon
  • 4. Big Pine Key
  • 5. Key West