It takes about three-and-a-half hours to reach Key West from the southern tip of mainland Florida, just south of Miami, at the start of The Florida Keys Scenic Highway. But with a chain of more than 800 islands and countless adventures in between, this getaway defines what it means to focus on the journey more than the destination. Slow down and stretch your road trip into a few days to discover everything the hidden Keys have to offer, including breathtaking natural scenery, charming bars and restaurants, vibrant culture, and rich history.
Along the way, explore a 100-year-old ghost town, a hidden beach, and wild birding paradise. In Islamorada, don’t forget to stop at one of the most impressive arts communities in The Keys (and order a creamy slice of Key lime pie). With a little digging, you’ll see that even the ever-popular Key Largo and Key West have uncharted corners left to uncover. Whether you’re looking for wide open spaces to snorkel or hike in peace or a secluded spot for a tiki drink, follow this guide to make the most of your trip.
The Upper Keys
Find tranquility beneath the waves. As the first undersea park in the country and the only living coral reef in the continental United States, John Pennekamp Coral Reef State Park ranks as an essential stop for many travelers. To enjoy its plentiful marine life without the crowds, book a private charter boat in Key Largo to whisk you to the sanctuary’s less-busy (but no less spectacular) snorkeling spots like Sea Gardens, Molasses Reef, Grecian Rocks, and White Banks. There you’re likely to see species like parrotfish, barracuda, sea turtles, rays, and pufferfish swimming peacefully among colorful corals.
Discover emerging talents. Morada Bay Arts and Cultural District in Islamorada—a village of six keys—distinguishes itself as the only true downtown area between Miami and Key West. Bustling with galleries and studio spaces, every third Thursday marks the district’s evening art walk. After admiring creative, nature-inspired prints, paintings, and ceramics at places like Redbone Gallery and Pasta Pantaleo’s Signature Gallery, sip an Iguana Bait or another signature microbrew at Florida Keys Brewing Company and drop by the historic Green Turtle Inn for one of the best slices of Key lime pie around.
Time travel. Abandoned over 100 years ago, Indian Key Historic State Park was once home to a thriving community of wreckers (people who salvaged goods off the ships that ran afoul of the nearby reefs). Today, its fascinating, eerily beautiful ruins—including warehouses, a saloon, a hotel, and a nine-pin bowling alley—are overgrown with tropical vegetation. During your visit, be sure to download the free narrated walking tour that details the rise and fall of the village and hike along its original paths. The journey to get there and back is just as fun. Rent kayaks from Robbie’s Marina—a contemporary Florida Keys landmark—and paddle out. Once you return, relax by the dock with a Trailer Trash Bloody Mary and beef jerky straw.
The Middle Keys
Land a trophy fish (or your dinner). Backcountry sport fishing and saltwater fly fishing may have been pioneered in Islamorada, but venture a bit further south, and you’ll find clear blue water with less competition and plenty of challenging sport fish like snapper, grouper, and mackerel available without going many miles offshore. At Hawks Cay Marina in Duck Key, lifelong fisherman Captain Dave Perry takes beginner anglers and experts alike blue water hunting in search of blackfin tuna, grouper, wahoo, and more. For a hyper-local meal, stop by Angler and Ale restaurant where the kitchen will blacken, grill, or fry your catch.
Befriend a dolphin. At the Dolphin Research Center on Grassy Key, guests can swim with a dolphin, shadow a researcher for a day, and observe dolphin and sea lion training sessions. With a focus on educational activities, research, and rescue, the 90,000-square-foot center was founded as a nonprofit corporation in 1984 and provides shelter for rescued and rehabilitated animals. Ready to meet more animals? At Aquarium Encounters in Marathon, come face-to-face with alligators, moray eels, turtles, tropical fish, and more aquatic creatures. Snorkel in a 200,000 gallon saltwater tank that hosts a diverse coral reef environment and hand feed sharks and cownose rays through a glass wall.
Go birding in the wilderness. A 63-acre oasis of nature trails, diverse ecosystems, and lush tropical trees, Crane Point Hammock provides the ideal birding conditions. Borrow a pair of binoculars from the visitor center and spy sea birds roosting out on Rachael Key, graceful herons and egrets along Rachael Creek, and songbirds in the forest canopy. You can also see many varieties of birds up close at the Marathon Wild Bird Center as they recuperate before being released.
Step back in time. There would be no modern Florida Keys without the engineering marvel that became the Seven Mile Bridge. Take a ferry out to Pigeon Key, now listed on the National Historic Register, where 400 workers lived during the construction of Florida tycoon Henry Flager’s Overseas Railroad linking mainland Florida to Key West. Guided tours of the scenic island leave three times a day and offer insight into the railroad’s past and the highway that travelers drive today. While you’re there, spend a couple hours snorkeling right off-shore where you’ll discover hundreds of fish and seagrass beds.
The Lower Keys
Bliss out at a hidden beach. Long considered one of the most stunning stretches of sand in The Florida Keys, Calusa Beach at Bahia Honda State Park offers excellent snorkeling, beachcombing, and sun worshipping. Best yet, because the island is virtually uninhabited, you’ll have no trouble finding a piece of paradise that’s all your own.
Paddle through the backcountry. Separated from crowd favorite Key West by a narrow channel, under-the-radar Stock Island has been growing more popular of late for its laid back vibe and calm, clear water. Check out its maze-like creeks on a backcountry mangrove boat tour with Namaste Eco-Excursions or rent a kayak or stand-up paddleboard at Lazy Dog Adventures and wind over seagrass beds and through tunnels of trees. Afterward, eat at Hogfish Bar and Grill, an open-air tiki bar and seafood joint with live music.
Search for old Key West. There’s more to Key West than the main tourist drag—and Shannon McRae, the general manager of Key West Food Tours, can help you tap into Key West’s bohemian spirit on her company’s bar crawl. Venture off legendary Duval Street and drink like a local at hidden gems like General Horseplay, Bad Boy Burrito, and First Flight Brewery.
Tour America’s most remote fortress. For many travelers, Key West marks their vacation’s last stop, but a road trip through The Florida Keys isn’t truly complete without visiting Dry Tortugas National Park (even if the islands are only accessible only by boat or seaplane). Hitch a ride on the Yankee Freedom ferry from Key West to Garden Key and tour Fort Jefferson, a colossal fortress originally built to help suppress piracy where nearly 2,000 people lived during the 1860s. With less than one percent of the park being on dry ground, you should also plan for a day of swimming, snorkeling, or diving in the crystal clear waters.