The Florida Keys stretch like a string of pearls across 113 miles of turquoise waters, connected by the iconic Overseas Highway. This island paradise blends natural beauty with quirky culture, creating an atmosphere unlike anywhere else in America.
The journey from Key Largo to Key West offers travelers a unique road trip experience where the destination truly is about the journey itself. Here is a list of 14 local stops that transform an ordinary drive into an unforgettable Keys adventure.
John Pennekamp Coral Reef State Park
America’s first underwater park sits at the gateway to the Keys in Key Largo. This 70-square-mile aquatic preserve protects vibrant coral reefs teeming with tropical fish. Visitors can take glass-bottom boat tours to view the underwater world without getting wet, or grab snorkeling gear to get up close with the colorful marine life.
The park’s famous underwater Christ of the Abyss statue stands in 25 feet of water, arms raised toward the surface in a serene pose. Many consider this stop an essential introduction to the Keys’ fragile ecosystem and a reminder of what makes this island chain truly special.
Alabama Jack’s
This no-frills waterfront eatery in Card Sound sits just before you officially enter the Keys. The open-air tiki hut setup offers fresh conch fritters and cold drinks with a side of authentic local atmosphere.
The weekend clogging dancers add a touch of quirky entertainment that feels perfectly in line with Keys’ culture. Motorcyclists, fishermen, and tourists all mingle at this beloved dive that’s been operating since 1947, creating a melting pot of characters you’d only find in the Keys.
The restaurant’s rustic wooden boards and weathered decor tell stories of hurricanes weathered and generations of patrons who’ve made this their first mandatory Keys stop.
Theater of the Sea
This family-owned marine mammal park in Islamorada has been operating since 1946. Unlike massive commercial aquariums, this intimate facility lets visitors swim with dolphins, sea lions, and rays in a natural lagoon setting.
The daily shows focus more on education than flash, giving guests genuine appreciation for these magnificent creatures. The lagoons utilize filtered seawater from the adjacent Florida Bay, creating habitats that closely mimic the animals’ natural environments.
The park’s longevity speaks to its conservation efforts and rehabilitation programs that have helped countless marine animals return to the wild over its 75+ years of operation.
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Robbie’s Marina
Feeding the massive tarpon that gathers at this Islamorada dock is practically a Keys rite of passage. For a few dollars, visitors buy buckets of fish to hand-feed these 100+ pound silver giants that leap from the water.
The surrounding market features local artists and crafts that make for unique souvenirs beyond the standard gift shop fare. The story behind this attraction adds to its charm – the first tarpon, named Scarface, was nursed back to health by the marina’s owners after being injured and soon brought friends that have remained for decades.
Watching newcomers squeal with delight (or terror) as these massive fish splash and compete for bait creates entertainment almost as good as the feeding itself.
Curry Hammock State Park
This hidden gem on Little Crawl Key offers a peaceful alternative to more crowded beaches. The shallow, protected waters make it perfect for kayaking through mangrove tunnels or paddleboarding across crystal clear flats.
The park’s isolation creates excellent stargazing opportunities on clear nights when the Milky Way stretches across the sky. Birdwatchers flock here during migration seasons when the park becomes a crucial stopover for hawks, falcons, and songbirds making their journey across the Gulf of Mexico.
The campground here ranks among the Keys’ best kept secrets, offering beachfront sites where campers fall asleep to gentle waves just steps from their tents or RVs.
Seven Mile Bridge
Driving across this engineering marvel between Knight’s Key and Little Duck Key creates an almost surreal experience. With endless blue stretching in all directions, it feels like flying above the water.
The old Seven Mile Bridge runs parallel to the new one, providing perspective on the incredible feat of connecting these islands long before modern construction methods. Fishing enthusiasts often park at either end to cast lines from the old bridge section, now converted to a walking and cycling path known as ‘Old Seven.’ Movie buffs might recognize segments of the bridge from action films like ‘True Lies’ and ‘License to Kill,’ where Hollywood explosions fictionally damage what hurricanes have tested for decades.
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Bahia Honda State Park
This park boasts what many consider the most beautiful beach in Florida. The powdery white sand and crystal clear waters create postcard-perfect views with the historic Bahia Honda Rail Bridge in the background.
The shallow sandbars extend hundreds of feet offshore, creating natural wading pools warmed by the tropical sun. The park’s beaches regularly win national awards and recognition from travel publications that rank it among America’s top coastal destinations.
Snorkelers can explore seagrass beds just offshore, where manatees occasionally graze, while history enthusiasts appreciate the remnants of Henry Flagler’s ambitious railroad that first connected these islands to the mainland.
National Key Deer Refuge
Big Pine Key hosts a population of miniature deer that stand just 24-32 inches tall. These adorable creatures, found nowhere else on Earth, often approach visitors without fear.
Dawn and dusk offer the best viewing opportunities when these diminutive deer emerge from the pine forests to forage along roadsides and in residential areas. The refuge was established in 1957 when the population had dwindled to just a few dozen animals, but conservation efforts have helped their numbers recover to around 800 today.
Drivers must exercise extreme caution on Big Pine Key, where reduced speed limits help protect these endangered animals that, unfortunately, don’t understand the dangers of crossing roads.
No Name Pub
This eccentric establishment on No Name Key began as a general store and bait shop in 1931 before evolving into a brothel and, finally, a pub. The interior walls and ceiling disappear beneath thousands of decorated dollar bills left by previous patrons.
Their stone-baked pizzas and fish sandwiches provide the perfect fuel for continued Keys exploration. Staff estimates that over $200,000 in singles now covers nearly every available surface, each bill representing someone’s visit to this off-the-beaten-path institution.
The pub proudly embraces its slogan, ‘A nice place if you can find it,’ referring to its location on an obscure island accessible only by a small bridge that many travelers miss entirely.
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Geiger Key Marina
This authentic ‘locals’ spot’ offers waterfront dining without the tourist markup or crowds. The tiki bar atmosphere and fresh-caught seafood provide a genuine Keys experience away from the main highway.
Their famous fish tacos pair perfectly with cold beverages as pelicans and egrets patrol the nearby docks. The surrounding RV park and marina create a tiny community where full-time residents mingle with travelers seeking long-term escape from northern winters.
Regular live music sessions feature local musicians who often incorporate conch shells and washboards alongside traditional instruments, embodying the quirky innovation that defines Keys’ culture.
Key West Cemetery
Established in 1847, this historic cemetery contains fascinating epitaphs reflecting the Keys’ colorful character. Famous inscriptions include ‘I told you I was sick’ and ‘At least I know where he’s sleeping tonight.’ The above-ground tombs, necessitated by the island’s rocky terrain, create an impressive city of the dead in the heart of Key West.
The 19-acre property contains an estimated 100,000 graves—far more than the current living population of the entire island. Self-guided tour maps highlight notable residents, including victims of the USS Maine explosion that sparked the Spanish-American War and the grave of a woman whose dying wish was to have her beloved pet poodle buried with her.
Fort Zachary Taylor
This Civil War-era fortress provides both historical interest and access to Key West’s best beach. The clear water offers excellent snorkeling right from shore, with tropical fish swimming among natural coral and limestone formations.
The massive brick structure itself provides a glimpse into 19th-century military engineering and strategic importance. During the Civil War, the fort remained in Union hands despite Florida’s Confederate allegiance, playing a crucial role in blockading southern shipping.
Archaeological work in the 1960s uncovered the largest collection of Civil War-era cannons in America, hidden inside the fort walls during renovations and now on display for visitors.
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Dry Tortugas National Park
Though requiring a side trip by ferry or seaplane, this remote island fort 70 miles west of Key West represents the ultimate Keys adventure. The massive Fort Jefferson sits surrounded by pristine waters with visibility often exceeding 100 feet.
The isolated location means uncrowded snorkeling among vibrant coral gardens rarely seen in more accessible locations. The fort served as a prison during and after the Civil War, most famously holding Dr. Samuel Mudd, who treated assassin John Wilkes Booth’s broken leg.
Overnight camping permits allow a fortunate few to experience star-filled skies unaffected by light pollution and sunrise beach strolls before day-trippers arrive.
Sunset at Mallory Square
Key West’s famous sunset celebration brings together street performers, artists, and food vendors each evening. While touristy, the event captures the island’s free-spirited essence as fire jugglers, tightrope walkers, and musicians entertain crowds gathered to watch the sun sink into the Gulf of Mexico.
The daily celebration transforms a simple sunset into a community event. This tradition dates back to the 1960s when locals began gathering to appreciate nature’s nightly show, gradually evolving into the carnival-like atmosphere found today.
Even repeat visitors find new characters each time, from the Cat Man and his trained felines to Dominique and his flying house cats, performers who have become local legends in their own right.
Island Heritage
The Keys have transformed dramatically since the railroad first connected these islands to the mainland in 1912. From isolated fishing communities to tourism hotspots, these islands maintain a distinctive culture despite increasing development.
The blend of natural beauty, quirky attractions, and laid-back atmosphere continues to draw visitors seeking experiences beyond ordinary vacations. The Florida Keys offer road-trippers a rare combination of accessibility and escape.
Each island along the Overseas Highway contributes its own character to this unique American paradise, where the journey truly becomes the destination.
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