Staycation Perfection: Drive Your Way Through Paradise

One of the world’s most renowned road trips is right here in the Florida Keys, cruising from one island to another along the Overseas Highway. South of Miami between Key Largo and Key West, this is the ideal staycation for adventure-loving families or couples seeking a romantic retreat closer to home.

The trip of over 100 miles takes around two to three hours non-stop. However, there’s so much to see and do, so take your time to soak up the spectacular scenery of the Sunshine State’s stunning island archipelago. Break up the journey with a stay at Tranquility Bay Resort, located halfway along the highway in the heart of the Keys.

Here are our tips for making the most of your drive on America’s easiest, breeziest highway, with plenty of pit stops to plan for along the way.

Ready, Set… Key Largo!

Once you’ve entered Key Largo, you’re officially in the Florida Keys with unbroken blue horizons of ocean and sky. Start your road trip with the right kind of fuel at some of Key Largo’s favorite dining spots, including Harriette’s Restaurant (Mile Marker 95.7) with its warm welcome, wallet-friendly prices and huge muffins. Also look out for Doc’s Diner (Mile Marker 99.6), popular among locals for its generous portion sizes including tropical French toast and breakfast burritos.

Next Stop: Islamorada

Continue your drive from Key Largo to Islamorada, which sits between the saltwater wilderness of the Everglades National Park and the deep waters of the Florida Straits. Stop at the Rain Barrel Artisan Village (Mile Marker 86.7), a fascinating sculpture art gallery featuring a giant fiberglass lobster at its entrance. There are individual shops all nestled under a canopy of giant Banyan trees selling unique homemade gifts, including unusual jewelry, pottery and ceramics.

Time to refuel again? It’s nearing lunchtime after all, and if there’s one place we recommend in Islamorada, it’s Lorelei (Mile Marker 82). As popular for its daytime menu as its evening sunset celebrations, this restaurant and Cabana bar offers one of the best views of Florida Bay while you savor seafood tacos or the ‘Lorelei’s World Famous Fish Sandwich,’ all washed down with an island drink.

Marathon or Bust

Carry on cruising down Highway 1 to the Middle Keys which are anchored by Marathon, a 10-mile-long island with a family-friendly reputation and a rich fishing heritage. Before checking in at Tranquility Bay, you will pass by popular attractions worth a visit. Take your pick from the Dolphin Research Center (Mile Marker 59) in Grassy Key where families can interact with and learn about exciting dolphin research. Also along the way is Aquarium Encounters (just after Vaca Cut Bridge at Mile Marker 53). Here, you will find an interactive Florida Keys aquarium experience with daily shark feedings, stingray encounters, and the opportunity to swim among fish on the attraction’s coral reef.

Or if you prefer an outdoor nature experience, nearby at Mile Marker 50 is Crane Point, a nature center with walking trails through a tropical hardwood grove. Right next door to Tranquility Bay is a wildlife lover’s paradise at the Turtle Hospital (Mile Marker 48.5) which is dedicated to helping injured sea turtles return to the wild. Then, relax and recharge at Tranquility Bay, the perfect spot for a memorable family vacation with a private beach, three pools, delicious dining and simple luxuries. You will soon feel a million miles away from reality.

Seven Mile Bridge

Halfway along the Overseas Highway, capture images of the impressive Seven Mile Bridge soaring over the Gulf of Mexico. Running alongside it is the Old Seven Mile Bridge, the hurricane-battered railroad built by Henry Flagler in the early 1900s which is now a popular spot for fishing. There are plenty of places to pull over and take some photos, take a stroll and watch the wildlife fly by.

The Lower Keys

The further south you drive, the more beautifully remote the scenery becomes in the Lower Keys. Stop in Big Pine Key (Mile Marker 29) and take a peaceful bicycle ride through Key Deer country. You can satisfy your sweet tooth further south in Sugarloaf Key at Mangrove Mama’s (Mile Marker 20) with a generous slice of Key lime pie on the sun-baked, palm tree-lined patio. Also worth a pit stop is Baby’s Coffee (Mile Marker 15), famous for its Cuban roasts and Key lime pie to-go.

As the afternoon starts merging into evening, your last leg of this world-renowned road trip will end in Key West just as sunset begins. The best spot to soak it up? Make your way to Mallory Square for Key West’s nightly Sunset Celebration with magicians, jugglers, musicians, artists and food vendors, all combining for an unforgettable cultural experience.

Ready to take to the road and staycate in style? View our helpful planning guide and special offers, including our Best Flexible Rate – perfect for if your plans may change – and book your idyllic Florida Keys vacation at Tranquility Bay.

Book online

Please be aware some of the restaurants and attractions mentioned above may be operating a limited service in line with social distancing guidance, or even temporarily closed. Please be sure to check online or contact the business directly for further information.