Tales and Stories and History From All The Keys

Florida Keys: A Story from Every Island – History, Legends & Hidden Gems

Discover the fascinating tales, hidden histories, and surprising facts behind each island in America's only living coral reef archipelago

The Enchanting Island Chain

The Florida Keys stretch 120 miles from the southeastern tip of Florida, forming a breathtaking archipelago of over 1,700 islands connected by the iconic Overseas Highway. Each island—or "key" (from the Spanish word cayo, meaning small island)—holds unique stories of pirates, pioneers, hurricanes, and Hollywood legends.

Whether you're a real estate investor exploring opportunities, a history buff, or a traveler seeking adventure, understanding the rich tapestry of stories woven into these islands transforms any visit from a simple vacation into a journey through time.

Table of Contents

SectionIslands CoveredUpper KeysKey Largo, Tavernier, Plantation Key, Windley Key, Upper & Lower MatecumbeMiddle KeysLong Key, Conch Key, Duck Key, Grassy Key, Key Colony Beach, MarathonLower KeysBahia Honda, Big Pine Key, Little Torch Key, Ramrod Key, Summerland Key, Cudjoe Key, Sugarloaf KeyKey West & BeyondStock Island, Key West, Dry Tortugas

Upper Keys

Key Largo – The Diving Capital of the World

Mile Marker: 106-91

Key Largo is the largest and northernmost island in the Florida Keys, spanning 33 miles of tropical paradise. Known as the "Diving Capital of the World," this island serves as the gateway to underwater adventures.

3 Fascinating Facts About Key Largo
FactThe Story🎬 Bogart Never Filmed HereDespite the 1948 film Key Largo starring Humphrey Bogart and Lauren Bacall being set on the island, not a single scene was actually filmed in the Florida Keys. The entire movie was shot on a Hollywood soundstage. The island capitalized on the fame anyway, and today the Caribbean Club bar claims to be the film's inspiration.🚢 The African Queen Lives HereThe original steamboat from the 1951 Humphrey Bogart and Katharine Hepburn classic The African Queen is permanently docked at the Holiday Inn Key Largo. Visitors can take canal cruises aboard this piece of Hollywood history for around $50 per person.🪸 America's First Underwater ParkJohn Pennekamp Coral Reef State Park, established in 1963, was the first undersea park in the United States. It protects 70 nautical square miles of coral reefs and is home to the famous 9-foot-tall Christ of the Abyss bronze statue submerged 25 feet underwater.

Real Estate Note: Key Largo offers diverse property options from waterfront condos to luxury estates, with median home prices significantly lower than Key West.

Tavernier – The Pirate's Landing

Mile Marker: 91-89

This small community sits between Key Largo and Islamorada, offering a quieter Keys experience with deep historical roots.

3 Fascinating Facts About Tavernier
- 🏴‍☠️ Named After Pirates: The island's name likely derives from the Spanish word taberna (tavern), referring to a pirate hangout that once existed here. Some historians believe buccaneers used this location to trade stolen goods with local fishermen.
- 🌊 The Hurricane That Changed Everything: The 1935 Labor Day Hurricane—still the strongest hurricane to ever make U.S. landfall with 185 mph winds—devastated Tavernier. The storm killed over 400 people, many of them World War I veterans working on the Overseas Highway.
- 🐊 Wild Tamarind History: Tavernier was originally called "Wild Tamarind" after the native trees abundant on the island. The area remained largely unpopulated until Henry Flagler's railroad brought development in the early 1900s.
Plantation Key – The Pineapple Paradise

Mile Marker: 90-86

Part of the village of Islamorada, Plantation Key earned its name from its agricultural past.

3 Fascinating Facts About Plantation Key
FactDetails🍍 Pineapple PlantationsIn the late 1800s, this key was home to thriving pineapple plantations. At its peak, the Keys shipped over 1 million crates of pineapples annually to northern markets before competition from Cuba and Hawaii ended the industry.🎣 Sport Fishing BirthplacePlantation Key is considered one of the birthplaces of sport fishing in America. In the early 1900s, wealthy industrialists discovered the incredible fishing here, establishing the Keys' reputation as a world-class angling destination.🏫 The Coral Castle ConnectionBefore settling in Homestead, Edward Leedskalnin—the mysterious creator of the Coral Castle—briefly lived in the Keys area. Legends persist that he developed some of his mysterious building techniques while observing coral formations here.
Windley Key – The Coral Quarry

Mile Marker: 85-84

This small but significant key holds geological treasures beneath its surface.

3 Fascinating Facts About Windley Key
- 🦴 Ancient Coral Walls: Windley Key is home to the Windley Key Fossil Reef Geological State Park, where visitors can walk through an ancient fossilized coral reef dating back 125,000 years. The walls of the old quarry expose cross-sections of pristine prehistoric coral.
- 🚂 Flagler's Quarry: Henry Flagler quarried keystone (fossilized coral rock) from Windley Key to build the foundations of his famous Overseas Railroad. The 8-foot-deep quarry walls still show the marks of early 20th-century equipment.
- 🎭 Theater of the Sea Origin: Theater of the Sea, opened in 1946, is the second oldest marine mammal park in the world. The flooded quarry pits from Flagler's railroad construction became the natural marine habitats used for dolphin and sea lion encounters today.
Upper Matecumbe Key – The Fishing Capital

Mile Marker: 84-79

The heart of Islamorada and the "Sport Fishing Capital of the World."

3 Fascinating Facts About Upper Matecumbe Key
FactThe Story💀 The Matecumbe MassacreIn 1840, a devastating raid by Seminole warriors during the Second Seminole War left the island's settlement destroyed. The attack was part of the broader conflict that made the Keys a dangerous frontier territory.🏆 World Record WatersThe waters surrounding Upper Matecumbe hold more IGFA (International Game Fish Association) world records than any other location on Earth. Legendary species caught here include bonefish, tarpon, permit, and sailfish.🌴 Presidential FishingFour U.S. Presidents have fished the waters of Islamorada: Herbert Hoover, Franklin D. Roosevelt, Harry Truman, and George H.W. Bush. The tradition of presidential fishing trips helped establish the Keys' elite reputation.
Lower Matecumbe Key – The Hurricane Memorial

Mile Marker: 79-73

This island bears the scars and memories of one of America's greatest natural disasters.

3 Fascinating Facts About Lower Matecumbe Key
- ⚰️ The Hurricane Monument: A stunning art deco monument stands as a memorial to the 400+ victims of the 1935 Labor Day Hurricane. The monument, featuring a palm tree being battered by waves, contains the cremated remains of over 300 victims—many of whom were never identified.
- 🚂 The Rescue Train That Never Made It: A rescue train was dispatched from Miami to evacuate workers before the 1935 hurricane struck. Tragically, the train arrived too late and was swept from the tracks by the 20-foot storm surge, becoming a twisted monument to the storm's fury.
- 🐢 Turtle Hospital Origins: Before the famous Turtle Hospital moved to Marathon, early sea turtle rehabilitation efforts in the Keys began in this area, as locals rescued turtles injured by boats and fishing gear in the shallow grass flats.

Middle Keys

Long Key – Zane Grey's Paradise

Mile Marker: 70-65

This slender island was once the exclusive retreat of America's most famous Western novelist.

3 Fascinating Facts About Long Key
FactDetails📚 Zane Grey's Fishing CampWestern author Zane Grey established a luxury fishing lodge on Long Key in the 1920s. Grey wrote several books here and set multiple fishing records. His camp attracted celebrities and millionaires until the 1935 hurricane destroyed it completely.🚂 Flagler's FavoriteHenry Flagler was so enchanted by Long Key that he built his personal fishing retreat here. The Long Key Fishing Club he founded attracted the era's elite, including President Herbert Hoover.🌉 The Bridge That Changed EverythingThe Long Key Viaduct—nearly 2.5 miles long—was an engineering marvel when completed in 1908. Its 180 concrete arches made it one of the longest bridges in the world and proved that Flagler's "Railroad That Goes to Sea" was possible.
Conch Key – The Tiny Treasure

Mile Marker: 63

One of the smallest inhabited keys, Conch Key offers a glimpse into authentic Keys living.

3 Fascinating Facts About Conch Key
- 🐚 Named for Conchs: The island's name comes from the queen conch (pronounced "konk"), a large sea snail that was once abundant in these waters. "Conch" also refers to native Keys residents—those born in the Keys are called "Conchs," while longtime transplants are "Freshwater Conchs."
- 🏠 Original Fish Camp: Conch Key was developed in the 1950s as a commercial fishing village. The original fish houses and docks remain, making it one of the most authentically preserved fishing communities in the Keys.
- 🌉 Two Bridges: Despite its tiny size, Conch Key is connected by two separate bridges—one on each end. This unique arrangement gives the small community two distinct entry points, unlike most Keys which have just one.
Duck Key – The Yacht Club Island

Mile Marker: 61

An upscale residential island with a colorful history of reinvention.

3 Fascinating Facts About Duck Key
FactThe Story🧂 Salt ManufacturingIn the 1800s, Duck Key was the site of salt manufacturing operations. Workers would flood shallow ponds with seawater and let the Florida sun evaporate the water, leaving behind valuable salt for food preservation.🏝️ Artificial IslandsFour of the five islands that make up Duck Key today are entirely man-made, created in the 1950s by dredging and filling. The development transformed a single small key into a multi-island residential community.🎬 Bloodline ConnectionDuck Key served as a filming location for the Netflix series Bloodline (2015-2017). The Hawks Cay Resort appeared throughout the series, showcasing the island's luxury atmosphere to international audiences.
Grassy Key – The Dolphin Sanctuary

Mile Marker: 60-57

Home to one of the world's most famous marine mammal rehabilitation centers.

3 Fascinating Facts About Grassy Key
- 🐬 Flipper's Home: The Dolphin Research Center on Grassy Key was originally founded as Santini's Porpoise Training School in 1958. Five dolphins from this facility starred in the TV series Flipper (1964-1967), making this the birthplace of one of television's most beloved animal stars.
- 🌿 Named for Seagrass: The island's name comes from the vast seagrass beds in the surrounding waters. These underwater meadows are critical nursery habitat for fish, shrimp, and the endangered West Indian manatee.
- 💔 Mitzi the Original Flipper: The original Flipper movie (1963) starred a dolphin named Mitzi, who lived at the Grassy Key facility. When Mitzi died, she was buried on the island, and her grave became an unofficial pilgrimage site for Flipper fans.
Key Colony Beach – The Golf Cart Paradise

Mile Marker: 54

A planned residential community with a distinctly different Keys vibe.

3 Fascinating Facts About Key Colony Beach
FactDetails🏌️ Man-Made ParadiseKey Colony Beach is almost entirely artificial, created in the 1950s by developer Phil Sadowski. Workers dredged fill material from Florida Bay to create new land, transforming a small mangrove island into a master-planned community.🛒 Golf Cart RequiredKey Colony Beach is famous for being a golf cart community. Residents and visitors navigate the small island primarily by golf cart, creating a relaxed, family-friendly atmosphere unique in the Keys.🌴 Independence DayKey Colony Beach incorporated as an independent city in 1957, making it one of the youngest municipalities in Florida. Despite having fewer than 1,000 full-time residents, it maintains its own city government and police force.
Marathon – The Heart of the Keys

Mile Marker: 54-47

The second-largest city in the Keys and the commercial hub of the island chain.

3 Fascinating Facts About Marathon
- 🏃 Running the Railroad: Marathon got its name from the exhausting, "marathon" effort required to build Henry Flagler's Overseas Railroad through this area. The construction camps here were among the most challenging on the entire route.
- 🐢 The Turtle Hospital: Founded in 1986, the Turtle Hospital in Marathon is one of the world's premier sea turtle rehabilitation facilities. The hospital has treated over 1,500 injured sea turtles, releasing most back into the wild. It operates from a converted motel—the turtles literally swim in renovated hotel pools!
- 🌉 Seven Mile Bridge: Marathon is the mainland anchor for the Seven Mile Bridge, one of the longest bridges in the world when completed in 1982. The original bridge, built for Flagler's railroad, still runs parallel and is used as a pedestrian and fishing pier called the Old Seven.

Real Estate Insight: Marathon offers more affordable real estate than Key West while providing full-service amenities including an airport, hospital, and major shopping centers.

Lower Keys

Bahia Honda Key – The Best Beach

Mile Marker: 37-36

Home to what many consider the most beautiful beach in the continental United States.

3 Fascinating Facts About Bahia Honda Key
FactThe Story🏖️ #1 Beach in AmericaBahia Honda State Park has been repeatedly named the best beach in the United States by Dr. Beach (Stephen Leatherman). Its natural, unmanicured shoreline and crystal-clear Caribbean waters make it uniquely beautiful.🌉 The Bridge on TopThe Bahia Honda Bridge is the only one on the Overseas Highway where the roadway runs on top of the railroad structure rather than on a separate deck. This creates the distinctive appearance of a bridge running over another bridge.🏝️ Deep ChannelThe name "Bahia Honda" means "Deep Bay" in Spanish. The deep channel between Bahia Honda and Spanish Harbor Keys made this a challenging location for bridge construction—and a popular anchorage for pirates in earlier centuries.
Big Pine Key – The Key Deer Kingdom

Mile Marker: 33-30

The second-largest island in the Keys and home to a beloved miniature deer species.

3 Fascinating Facts About Big Pine Key
- 🦌 The Smallest Deer: Big Pine Key is the primary home of the Key deer, a subspecies of the white-tailed deer that stands only 24-32 inches tall—about the size of a large dog. With fewer than 1,000 individuals remaining, they're one of America's most endangered mammals.
- ⛪ The Blue Hole: A former limestone quarry on Big Pine Key filled with fresh groundwater to create the Blue Hole, the only significant freshwater lake in the Keys. This unexpected oasis attracts alligators—the only place in the Keys where they can survive—along with turtles and rare birds.
- 🔦 No Streetlights: Big Pine Key is the largest "dark sky" community in the Florida Keys. The island prohibits streetlights to protect nesting sea turtles and the endangered Key deer, creating remarkably dark skies for stargazing.
Little Torch Key – The Secret Luxury

Mile Marker: 29-28

A small key hiding one of the Caribbean's most exclusive resorts.

3 Fascinating Facts About Little Torch Key
FactDetails🏝️ Little Palm IslandLittle Torch Key is the jumping-off point for Little Palm Island Resort, accessible only by boat or seaplane. This ultra-exclusive resort has hosted presidents, celebrities, and dignitaries seeking complete privacy—with room rates exceeding $2,000 per night.🌲 Named for TorchwoodThe island's name comes from the torchwood tree (Amyris elemifera), whose resinous wood was historically used to make torches. Early settlers burned torchwood for light and to repel mosquitoes.🚢 Submarine SightingDuring World War II, German U-boats were spotted in the waters near Little Torch Key. The Keys' position made them strategically important, and locals reported numerous submarine sightings throughout the war.
Ramrod Key – The Tropical Fish Capital

Mile Marker: 27

A quiet residential key with an unusual claim to fame.

3 Fascinating Facts About Ramrod Key
- 🐟 Tropical Fish Industry: Ramrod Key was once the center of the Florida Keys' tropical fish collection industry. Divers here harvested ornamental fish for aquariums worldwide, creating a unique local economy before regulations limited the practice.
- 📛 Mysterious Name: The origin of "Ramrod Key" is debated among historians. Some believe it refers to the ramrod tools used in old muskets, while others suggest it comes from a long-vanished shipwreck or possibly a local plant with rod-like branches.
- 🌊 Looe Key Access: Ramrod Key provides the primary access point to Looe Key National Marine Sanctuary, one of the most spectacular coral reef diving sites in North America. The reef is named after HMS Looe, a British warship that sank here in 1744.
Summerland Key – The Sponge Diver's Haven

Mile Marker: 25

A residential island with deep roots in the sponge industry.

3 Fascinating Facts About Summerland Key
FactThe Story🧽 Sponge Diving CenterSummerland Key was a major sponge diving center in the late 1800s. Greek and Cuban divers harvested natural sponges from the surrounding waters, shipping them to markets in Key West and New York.✈️ The Bat TowerOn neighboring Sugarloaf Key, the famous Perky Bat Tower was built in 1929 to attract bats that would control mosquitoes. The bats never came, but the 35-foot tower still stands as a monument to eccentric pest control—visible from Summerland Key.🏠 No Commercial ZoneUnlike many Keys, Summerland has very limited commercial development. This was largely intentional—early developers marketed it as a peaceful residential retreat away from tourist traffic.
Cudjoe Key – The Blimp Base

Mile Marker: 23-21

Home to a surprising piece of national security infrastructure.

3 Fascinating Facts About Cudjoe Key
- 🎈 Fat Albert Lives Here: Cudjoe Key hosts "Fat Albert", an aerostat radar blimp operated by the U.S. military. The tethered balloon rises 10,000-15,000 feet to detect low-flying aircraft and vessels, particularly monitoring for drug trafficking from the Caribbean. https://agentsgather.com/tales-and-stories-and-history-from-all-the-keys/