Florida Keys Road Trip: Fuel up for reef dives, boat rides, and sunset seafood feasts along the 113-mile-long Overseas Highway. The Florida Keys have long attracted visitors looking for sunshine and old Florida flair. The 125-mile string of islands is an open-air playground, home to ten state parks, two national parks, and a designated marine sanctuary. Here, you can snorkel the world’s third-largest barrier reef, sip daiquiris at the former Hemingway haunts, and crack a plate of stone crab through mangrove thickets via kayak. Consider a trip to the Keys akin to jetting off to the Caribbean – without packing your passport.
“There is something here for everyone,” says Linda Ann Luiza, a Virtuoso travel consultant and boat captain living in the Keys. “Fishing, diving, kayaking, and other water sports — plus a huge cultural arts scene, fascinating and true tales of shipwrecks, and more.” Perhaps her favorite aspect of calling it home: the happy-go-lucky vibe of the locals.
A road trip is the best way to pick up as many keys as possible. From the mainland, jump onto the Alien Highway: U.S. This southernmost leg of Route 1 travels from Key to Key West via 42 bridges. While it spans only 113 miles, the plentiful turns and adventure activities can easily stretch the trip over the course of a week. (Less car time, more sunshine – ideal road trip, right?)
Florida Keys Road Trip
Days 1-2: Key Largo
Grab your reef-safe sunscreen and dive in.
The drive from Miami to Key Largo takes approximately 45 minutes. Upon arrival, prepare to become acquainted with one of the Keys’ best assets – the waters that surround them. Key Largo provides prime access to the Florida Reef, the world’s third-largest coral barrier reef, a designated National Marine Sanctuary that locals and conservationists are passionate about preserving. Florida Keys Road Trip.
Water World: “Snorkeling or diving at John Pennekamp Coral Reef State Park is a can’t-miss experience,” says Stephanie Fisher, a virtuoso consultant who lives in the Keys. “Its underwater Christ of the Abyss statue is incredible.” Join the Coral Restoration Foundation, an organization dedicated to rehabilitating endangered reefs, on a diving or snorkeling excursion to help monitor corals.
Hidden Gem: Stop by the Laura Quinn Wild Bird Sanctuary, a haven for unmissable avians just off mile marker 92. (Pro tip: Locals use green mile markers along Overseas Highway to give directions more than using street addresses.) Visitors can. Learn about the center’s rescue work and feed the resident brown pelicans.
Days 3-4: Islamorada
Embrace island time and catch a sunset – or two.
Comprised of six smaller islands, Islamorada lays claim to being the “sportfishing capital of the world”. Even if trophy catching isn’t your thing, it’s laid-back dining (add Hungry Tarpon and Florida Keys Brewing Company to your list) and cinematic panoramas (Netflix’s Bloodline was filmed here) make it the night. Worth making.
Must do: get on the boat! Islamorada has the world’s highest concentration of charter-fishing outfitters, so your virtuoso consultant can easily arrange an outing that’s right for you, whether it’s an onshore jaunt to catch Tarpon or deep in the Gulf of Mexico Take a sea tour. Cast for Sailfish, Marlin, and Tuna. Daily boat tours depart to explore the surrounding flats and head out to Everglades National Park, which celebrates its 75th anniversary this year.
Hidden Gem: Lignumvitae Key Botanical State Park, on a small island across from mile marker 78, is accessible only by boat or kayak. Head there for an afternoon hike through a tropical hardwood hammock (a closed-canopy forest habitat) and look for manatees just offshore.
Day 5: Marathon
Will brake for beaches, sea turtles, and history.
Smack in the middle of the Keys, Marathon consists of several small islands that span between mile markers 60 and 47. There is so much to explore from family-friendly beaches to waterfront restaurants with some of the best seafood in the area.
Don’t Miss: Turtle Hospital is the only veterinary center in the world dedicated to sea turtles. The nonprofit opened in 1986 and has since helped rehabilitate and release more than 1,500 turtles. Visitors can tour the hospital and learn more about its work and, if they’re lucky, see a loggerhead turtle being released on a nearby beach.
Island Connection: In the early 1900s, the men who built Henry Flagler’s Florida East Coast Railway (and its original Seven Mile Bridge) lived on Little Pigeon Key, a small island just below the bridge. Today, travelers can learn about life in the Keys more than a century ago during a tour of the five-acre island, accessible only by ferry.
Day 6: The Lower Keys
Take a walk on the wilderness side.
On the way out of the marathon, as you head for the Lower Keys, you’ll hit the most iconic part of your drive: the Seven Mile Bridge. Completed in 1912, the original bridge was destroyed by a storm in 1935 (part of it now serves only as a pedestrian pier, reopening in January after four years of renovations). Once across the bridge, you’ll reach 35-miles of tiny islands, known as Lower Key, which are home to some of the most off-the-beaten-edge fun in the region.
A must-see, according to both Fisher and Luiza, is the National Key Deer Refuge on Big Pine Key, home of the endangered endemic (and adorable) Key Deer.
Don’t Miss: Big Pine Key’s Bahia Honda State Park and a pair of palm-fringed beaches, Loggerhead and Calusa. For happy hour, head to local favorite No Name Pub, a former general store, and brothel known for plastering more than 80,000 one-dollar bills on its walls. “I love this place because it’s an old-timer key,” says Luiza. “And they have great pizza and cold beer.”
Hidden Gem: Spend an early morning sea kayaking around Stock Island, an under-the-radar spot that has a small and eclectic arts community across the Channel from Key West. After paddling through the mangrove thickets, break for a pint of Kalik and a grilled snapper sandwich at Hogfish Bar & Grill, a kitschy open-air restaurant on the island.
Days 7-8: Key West
Channel Hemingway in the Conch Republic.
Key West packs in a plethora of culture, cocktail bars, and history into its small, two-by-four-mile spread. You can’t leave without spending at least a full day here, where the pastel cottages have some of the Keys’ most colorful stories.
Don’t Miss: The Ernest Hemingway Home and Museum, a former retreat of the literary legend who lived and wrote here in the 1930s. The immaculate interiors of the Spanish Colonial mansion are a treat for both Hemingway fans and design lovers; In the surrounding gardens, everyone will love to run into one of the 60 or so six-legged cats, believed to be the descendants of the author’s own pet.
Botanical Break: Off Duval Street, The Key West Butterfly & Nature Conservatory offers a Zen-inspired experience among more than 50 species of butterflies. “Be sure to request a guided tour,” says Luiza. “I love it because you get to see the metamorphosis from larva to butterfly.”
When it’s time to go home, you have two options: leave your rental car and exit Key West Airport, or head back to Miami, which is a four-hour drive from Key West. Either way, we recommend making at least one more stop for a slice of Key Lime Pie.
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