Discover Florida Keys: A Self-Guided Tour

Drive the Overseas Highway through the Florida Keys on this self-guided tour spanning sixty stops from Key Largo to Key West. Cross forty-two bridges including the iconic Seven Mile Bridge, explore the only living coral barrier reef in the continental United States, and discover islands rich with pirate lore, Hemingway legend, and Conch Republic spirit. Your guide follows the Mile Marker system from one hundred twenty-six to zero, visiting John Pennekamp State Park, seeing giant tarpon at Robbie's, observing rescued sea turtles in Marathon, and spotting endangered Key deer on Big Pine Key. In Key West, explore Hemingway's home with its famous six-toed cats, watch the sunset at Mallory Square, and walk Duval Street from the Gulf to the Atlantic. Includes Flagler's railroad history, the eighteen thirty-five hurricane, Cuban cigar heritage, and tips for world-class snorkeling and diving along the reef. Perfect for road trippers and island lovers alike.

1. 1

   Key Largo

   1 hour

   Welcome to the first and largest island of the Florida Keys. Key Largo sets the tone for the entire journey with its lush tropical atmosphere, roadside seafood shacks, and waterfront marinas. Your audio guide begins here, covering the history of the Overseas Highway and what lies ahead on one of America's most iconic road trips.

2. 2

   Christ of the Deep

   Pass by

   Just offshore from Pennekamp, an eight-and-a-half-foot bronze statue of Jesus rests nine feet below the surface in the Key Largo Dry Rocks reef — one of the most photographed underwater sites in the world. Your audio guide shares the Italian origins of this iconic statue and its symbolism for divers worldwide.

3. 3

   Islamorada

   1 hour

   A hidden gem in the Upper Keys, Anne's Beach is a free, award-winning natural beach featuring a wooden boardwalk through a mangrove wetland. Named after environmental activist Anne Eaton, it offers calm, shallow waters ideal for wading and relaxing — a perfect free stop to stretch your legs.

4. 4

   Stop 4

   1 hour

   Stand at a solemn roadside monument honoring the 408 lives lost in the most powerful hurricane ever to strike the United States — a Category 5 storm that obliterated Henry Flagler's Overseas Railroad. Your audio guide recounts the devastating storm surge and the doomed rescue train that arrived too late.

5. 5

   Seven Mile Bridge

   30 min

   Cross one of the most iconic bridges in America, stretching nearly seven miles above open water with the turquoise Gulf of Mexico on one side and the deep blue Atlantic on the other. The historic Old Seven Mile Bridge runs alongside it — the original Flagler-era railway bridge featured in the film True Lies. Your audio guide covers the engineering marvel and its construction history.

6. 6

   Bahia Honda State Park

   Pass by

   One of the most beautiful beaches in the southeastern United States, Bahia Honda offers powder-white sand, protected shallow waters ideal for snorkeling, and breathtaking views of the historic Old Bahia Honda Bridge.

7. 7

   Key West Historic Seaport

   1 hour

   Wander the southernmost city in the continental United States, soaking in the pastel-painted Conch houses, vibrant street art, and Caribbean energy of Old Town. Your audio guide covers Hemingway's six-toed cats at his home on Whitehead Street, the Truman Little White House, and the storied bars of Duval Street.

8. 8

   Mallory Square

   1 hour

   End your journey the Keys way — with the legendary nightly sunset celebration at Mallory Square. Street performers, local artists, food vendors, and hundreds of fellow travelers gather every evening to toast the sun as it sinks into the Gulf of Mexico.

9. 9

   Duval Street

   30 min

   Walk the famous "mile and a quarter" of Duval Street from the Gulf to the Atlantic, ending at the iconic red, black, and yellow Southernmost Point buoy — just 90 miles from Cuba and the perfect final photo of your Keys adventure.

10. 10

    Dry Tortugas National Park

    Pass by

    We coversthis remote national park located 70 nautical miles west of Key West, where the massive Civil War-era Fort Jefferson rises dramatically from the sea. The Dry Tortugas offer some of the most pristine snorkeling in the Caribbean and extraordinary birding during spring migration — a worthy overnight extension for adventurous travelers.

• Not recommended for travelers with spinal injuries
• Not recommended for travelers with poor cardiovascular health
• Public transportation options are available nearby
• Suitable for all physical fitness levels

For a full refund, cancel at least 24 hours before the scheduled departure time.