The Ultimate Guide to a Florida Keys Road Trip Adventure

Fact checked by Elizabeth MacLennan

A drive down Florida’s Overseas Highway from Key Largo to Key West offers the perfect blend of eccentric bohemia and chic joie de vivre. As the mile markers decrease, Old Florida charm sharpens into focus. Strip malls hawking beach sundries and snorkeling tours along the upper reaches of U.S. 1 give way to dazzling turquoise flashes as the road becomes more bridge than highway. The route south is festooned with the Keys’ ubiquitous kitsch — a giant, spiny lobster presides over a local arts village, lipsticked manatees clutch mailboxes, and hand painted mermaids tempt passersby with the promise of sunset cocktails.

You could drive the 113-mile stretch in a little over three hours; however, why would you want to? Road trips, especially one as iconic as this, are all about the stops along the way. So put the top down and cue Jimmy Buffet. Here’s our guide to the best the Florida Keys has to offer.

Key Largo

Ease yourself into the Keys’ laidback vibe just south of Homestead with a detour onto Card Sound Road. A stop into Alabama Jack’s is a must, especially if you’re a first-timer. The scrappy, waterside seafood shack has been the Keys’ unofficial welcome wagon since 1947 and serves some of the best conch fritters around. Live music and the line of Harleys outside add to the honky-tonk scene.

With your internal clock synced to island time, cruise over Card Sound Bridge and into Key Largo where you’ll find John Pennekamp Coral Reef State Park at mile marker 102.5. Explore the park’s prolific marine life and a portion of the 360-mile Florida Reef Tract — North America’s only living coral barrier reef — on a guided snorkeling tour. Or rent kayaks and head out for a paddle through miles of mangrove-lined wilderness trails.

Key Largo is at the epicenter of sustainability efforts in the Florida Keys, especially concerning reef health. At the Coral Restoration Foundation, researchers are rearing and planting corals in undersea nurseries. For a unique experience, snorkelers and divers looking to add an eco-tourism stint to their travels can assist scientists with outplanting and reef monitoring at active restoration sites.

After a day of sea and sun, check into the breezy Baker’s Cay Resort, a lush retreat tucked into a secluded setting with gorgeous Florida Strait views. The resort partners with local environmental organizations to create eco-friendly guest programming. It was also the first resort in the Keys to join Reef Relief’s “Skip the Straw” campaign.

Islamorada

You could easily spend a few days hopping around the string of tiny islands that make up Islamorada; moreover, The Moorings Village is the perfect place to call home.

Built on a former coconut plantation, the resort is home to eight private cottages nestled amidst tropical landscaping just steps from the Atlantic. Eight-hundred palm trees dot the property, and there’s no shortage of hammocks for lounging beneath the verdant fronds.

Grab a paddleboard and head out for an ocean jaunt, watch the world go by from the cool shade of your porch, or while away a few hours by the gorgeous pool. If you can tear yourself away, single-speed beach cruisers are available for a pedal around town. Check out the galleries around the corner in the Morada Bay Arts and Cultural District — every third Thursday is the district’s evening art walk — or pop into the beer garden at the Florida Keys Brewing Company for a hyper-local tasting flight.

Robbie’s Marina, one of the Florida Keys’ most iconic landmarks, sits on the tip of Lower Matecumbe Key, about five miles south at mile marker 77.5. The epitome of the archipelago’s barefoot affability, Robbie’s is a waterside shantytown of sorts that includes an outdoor marketplace, a marine sports outpost, and the Hungry Tarpon restaurant, named for the school of enormous silver fish that have been circling the docks for decades. Seven bucks will get you a bucket of bait and admission to the dock, and feeding the leaping, thrashing creatures provides a memorable diversion.

Afterwards, head out for an eco-tour through Islamorada’s pristine waters with Captain Sam Zeher or just chill dockside with one of Robbie’s Trailer Trash Bloody Marys, complete with a beef-jerky straw.

When the dinner hour beckons, shake the sand from your toes and head to Pierre’s, an elegant plantation-style house with a wide verandah overlooking Florida Bay. A few miles north at Marker 88, the chef serves the kind of super-fresh seafood one would expect to find in the sportfishing capital of the world. Tuck into cracked coconut-crusted shrimp and fresh Florida lobster on the outdoor patio with a glass of fruity Chardonnay — for a relaxed joint, Marker 88 has an excellent wine list. At either spot, the famous Keys sunset is guaranteed to put on a memorable show.

Marathon

Even before Hemingway’s old man took to the sea, the Keys were a saltwater angler’s paradise, legendary for big game like sailfish, wahoo, and blue marlin. Though pulling a trophy fish from the ocean can be a thrill, sometimes the best part of casting a line is eating your catch later.

One of the best ways to do so is on a hook-and-cook adventure at Hawks Cay Resort on Duck Key, a pocket-sized island about 20 miles south of Islamorada. When it comes to relaxation, the resort offers a stunning adults-only enclave called Oasis Cay.

Get out onto the water with lifelong conch (i.e., Florida Keys native) Captain Dave Perry, who has been fishing the Keys for decades and runs charters out of the Hawks Cay Marina with Captain Justin Brunk. In addition to blue water hunting, the two specialize in fishing the reef for snapper and grouper, fish that can later be blackened, grilled, or fried for a hyper-local meal at Angler and Ale, the resort’s dockside restaurant.

Connecting Marathon to the Lower Keys, the Seven-Mile Bridge is a highlight of any Keys road trip; therefore, driving it feels like being immersed in an ocean-themed movie. But before you do, take a ferry out to picturesque Pigeon Key for a dose of Keys history.

In the early 1900s, Florida tycoon Henry Flagler envisioned an Overseas Railroad linking mainland Florida to Key West. The project was nicknamed Flagler’s Folly — no one believed his ambitious plan would come to fruition — yet, despite naysayers, the rail line was finished in 1912 complete with the engineering marvel that became the Seven-Mile Bridge. During the railroad’s construction, more than 400 workers lived on Pigeon Key, which is now listed on the National Historic Register. Tours of the tiny island leave three times daily from the Pigeon Key Visitor’s Center and offer a deep dive into the story of the railroad, its ill-fated demise, and the scenic highway travelers drive today.

The Lower Keys

Take a detour for some beach bliss at Bahia Honda State Park, a 524-acre swath of nature tucked between the Atlantic and the Gulf. Don’t forget to drop by Sandspur Beach, long considered one of the best in the Keys.

On Big Pine Key, stop into the new Florida Keys National Wildlife Refuges Nature Center, which features exhibits spotlighting the Keys’ four wildlife refuges including the nearby National Key Deer Refuge. Established in 1957, the refuge protects approximately 9,200 acres of land on Big Pine and No Name Keys that serves as habitat for endangered Key Deer. Stick to the speed limit around here — the diminutive creatures have been known to dart into the road, especially at dawn and dusk.

About 30 minutes south, you’ll find authentic, Old Keys spirit on the docks of Geiger Key Marina at The Fish Camp. Founded by local restaurateurs Michelle and Bobby Mongelli, also behind the well-loved Hogfish Bar and Grill on nearby Stock Island, this open-air tiki bar and seafood joint claims to be on “the back side of paradise,” which certainly feels accurate when you’re sitting waterside with a plate of succulent Key West pink shrimp and a cold beer. The Sunday afternoon barbecue is legendary.

Head out to explore the labyrinth of waterways around Stock Island on a guided kayak tour with Lazy Dog Adventures. Trips leave from a tiny inlet on Cow Key Channel and wind through the mangrove tunnels and saltwater creeks hugging the edge of the Atlantic. The vibrant ecosystem provides a habitat for manatees, sea stars, tropical fish, and all kinds of shorebirds — many of which you’ll encounter while paddling through the Keys’ backcountry wilderness.

Key West

Key West exudes the same anything-goes bonhomie it did back in the day of rumrunners and speakeasies — only now it’s infused with a shot of modern flair. Colorful conch cottages line the streets of Old Town, swank cocktail salons mingle with celebrated watering holes on Duval, and feral fowl give new meaning to free-range as they strut along the sidewalks crowing with carefree abandon. The destination also has an eclectic mix of top-rated hotels to suit every traveler.

Find respite from the downtown bacchanalia at the Parrot Key Hotel and Villas. The entire property breathes Old Key West charm. Walkways edged with white-picket fences wind through tropical gardens past hidden swimming pools and quaint, two-story clapboard bungalows. Bright-blue Adirondack chairs sit on covered porches, hammocks swing beneath shady palms, and ceiling fans spin lazily overhead at The Grove, the resort’s new open-air restaurant. Parrot Key’s complimentary shuttle delivers guests throughout the day to either a private beach club at Smathers Beach or to the heart of Old Town. For a DIY adventure, a fleet of single-speed beach cruisers invites exploration.

At four miles long and two miles wide, Key West is made for biking. Pedal through dappled sunlight along Whitehead Street to the Ernest Hemingway Home and Museum. Inside, passionate docents supply a glimpse into the profound yet tragic genius of one of the Lost Generation’s most colorful characters. Pay further tribute to Papa at the Hemingway Rum Company, which produces the award-winning Papa’s Pilar, named for the author’s beloved fishing boat. The company’s flagship headquarters, housed in a former tobacco warehouse, is part distillery, part tasting room, and part museum. Find a spot at the bar and sample delicious, dark and blonde Solera-blended rums amidst all variety of Hemingway-themed ephemera.

When the sun starts to set, climb aboard Danger Charters‘ elegant, three-masted schooner for a wine-tasting sail that offers a polished alternative to the nightly circus — think fire juggling acrobats and hoop-jumping cats — at Mallory Square. Or take a quick jaunt on the private ferry to Sunset Key for a gastronomical adventure overlooking the Gulf of Mexico at Latitudes, the signature restaurant at Sunset Key Cottages. There, you’ll dine on yellowtail, grouper, or cobia by the light of tiki torches with your toes in the sand. Innovative cocktails, crisp white tablecloths, and dreamy island views round out a memorable evening.