Leaving the traffic and skyscrapers of Miami you enter the land of flip-flops and island time. The Atlantic Ocean licks the narrow string of islands to the south while the Gulf of Mexico kisses the north side. The only agenda item on your calendar is to witness the sunset with a cocktail in hand. Welcome to the Florida Keys!
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What are the Florida Keys?
The Florida Keys consists of a string of tropical islands stretching 120 miles off the southern tip of Florida. Marking the southernmost continental point in the United States, Key West. Renowned for its outdoor activities.
The islands were historically well located for trade with Cuba and the Bahamas and offered the main trade route from New Orleans. This and many other notes in history have made the islands witness to a colorful history.
Discovery of the Florida Keys
Most believe the Keys were discovered around 1513 by Ponce de Leon for the Spanish. He named the area “Los Martires” (“The Martys” since they looked like suffering men from a distance). You can find Historical Marker 50 noting his discovery at 1405 Duval Street.
Overseas Railway: Connecting the Florida Keys to the Continental United States.
The Florida Keys were long accessible only by water, but that changed with Henry Flagler’s Overseas Railway in the early 1910s. Initially called “Flagler’s Folly,” the progress was disrupted by 3 hurricanes (1906, 1909, 1910) and required many engineering innovations. At one time during construction more than four thousand men were employed with a project cost of more than $50 million (in the early 1900s).
Despite all the issues, the final link of the railroad at Trumbo Point was completed in 1912. Henry Flagler made the first trip on the railroad that linked the entire east coast and became known as the “Eighth Wonder of the World.” The railroad continued with a disappointing traffic volume until much of it was destroyed in the Labor Day Hurricane of 1935.
The Caribbean Club
Opened in 1938, this is the oldest bar in the Upper Keys and one of the oldest relics of Key Largo. The club was made famous for the exterior shots in the 1948 film, Key Largo starring Humphrey Bogart and Lauren Bacall.
Pennekamp State Park
The first underwater park in the United States, John Pennekamp State Park includes approximately 70 nautical square miles of adjacent Atlantic Ocean waters. Added to the National Register of Historic Places on April 14, 1972, the primary attraction is the coral reefs and associated marine life. Other notable features are the Christ of the Abyss and the Visitor Center’s 30,000-gallon saltwater aquarium (and six smaller aquariums).
Florida’s Christ of the Abyss
Standing nine feet tall in the 25 feet of water off the coast of Key Largo stands the Christ of the Abyss or Christ of the Deep. Submerged in John Pennekamp State Park, the statue is the third cast from the original Italian mold by Guido Galletti. And serves as a memorial to all those who have lost their lives by the sea. The piece was donated to the Underwater Society of America by the Italian dive equipment manufacturer Egidio Cressi.
Lowered on August 25, 1965, the artwork quickly became one of the most famous underwater attractions in Key Largo. The top of the statue sits around eight to ten feet below the surface, making it visible to snorkelers.
History of Diving Museum
The small not-for-profit museum has tirelessly collected everything diving-related you can image.
Spiegel Grove Wreck Dive
Sunk on June 10, 2002, but Hurricane Dennis turned the ship upright in July 2005. The ship was sunk by the state of Florida to make an artificial reef off Key Largo. Divers enjoy the artificial reef today.
African Queen
Immortalized in the 1951 Humphrey Bogart and Katharine Hepburn movie of the same name is now a working tour boat at Mile Marker 100. The once cargo ship was discovered by John Hutson during a hunting trip. Decided it would be great for the film; however, after its silver screen appearance, it was returned to regular service. Until 1968, when it was re-discovered half sunk in Cairo, Egypt, and towed back to the US for restorations. Today you will find it nestled between rows of newer million-dollar yachts, but still a classic.
Labor Day Hurricane of 1935
Monday, September 2, 1935
The US government employed World War I veterans. In an effort to complete highways bridges were to be constructed to connect the entire Florida Keys. The program was a part of the government relief program resulting from the Great Depression. The workers were housed in ramshackle buildings dispersed among three construction camps in the Upper Keys. However, when the evacuation train failed to reach the area more than 200 perished when the Category 5 hurricane hit the islands. The hurricane made landfall near Islamorada. It is one of four Category 5 hurricanes to make US landfall since weather records began in 1850.
The lives lost are memorialized at Mile Marker 82.
The storm also ended the 23-year run of the Overseas Railway. The damaged tracks were never rebuilt. The Overseas Highway replaced the railroad as the main transportation from Miami to Key West.
Crane Point Museum & Nature Center
Tucked into the heart of Marathon Key is a well-kept secret of the Florida Keys. Crane Point is a 63-acre tropical oasis of trails and educational displays. The area was home to a Bahamian immigrant and his family in the early 20th century. George Adderly and his family made a living selling charcoal and sponges (gathered from the sea). Their home remains for visitors to see their way of life today.
The Marathon Wild Bird Center is located in the area as well. The center is a hospital for injured pelicans, egrets, and other Keys birds.
Dolphin Research Center
Operating as a nonprofit education and research center, where you get the chance to learn about dolphins up close! Whether you chose the behavior sessions, educational presentations or trainer-assisted swims you are sure to make memories to last a lifetime!
No Name Pub
Dating back to a 1931 general store, the now pub is a right of passage for visitors. Watch for the local key deer while winding through the roads looking for this off-the-beaten-path pub.
Turtle Hospital
Housed at the former Hidden Harbor Motel, the hospital is the first sea turtle veterinary hospital. The non-profit operates as a rescue and rehabilitation for sea turtles but allows visitors. Visitors to the hospital will take a 90-minute educational tour. Where they will learn about dangers to sea turtles, view 100,000-gallon saltwater pool, visit hatchlings and even feed the turtles.
Book your tour here or adopt a sea turtle for $35 a year here.
Robbie’s
Grab your photos while feeding the tarpon at Robbie’s! Kneel on the dock while holding the minnow just above the surface and the large tarpon will leap from the water to snatch the minnow.
Travel the Seven Mile Bridge
Connecting Knight’s Key and Little Duck Key, the Seven Mile Bridge is actually 6.79 miles (35,862 feet) long. Making it one of the longest bridges in the world when it was built. Travelers are able to see two bridges here. The modern bridge is open to vehicular traffic. While the neighboring older bridge (the former Overseas Railroad) is open to pedestrian traffic only. The new bridge is a box-girder structure made of precast, prestressed concrete sections. Near the center the bridge arcs to provide a 65-foot boat clearance.
Runners mark your calendars! Each April the bridge is closed for the Seven Mile Bridge Run
The bridge has been featured in many films such as License to Kill, True Lies, 2 Fast 2 Furious, and Burn Notice.
Pigeon Key
Pigeon Key served as the base camp during the construction of the Seven Mile Bridge.
Today you can still see a few of the original structures that housed more than 400 bridge workers. The Pigeon Key Museum and Marine Science Center have exhibits dedicated to the builders of the “Railroad that Went To Sea.” The displays offer a glimpse of what life was like for the railway workers and for those maintaining the railroad until 1935.
The Conch Republic: Succession from the United States
For a few minutes in 1982, Key West seceeded the United States. The seccession was in response to the US Border Patrol establishing a roadblock and inspection points on US Hwy 1. Stopping all northbound traffic to the mainland and disrupting tourism. The inspections were intended to find illegal drugs and undocumented immigrants.
The Key West City Council repeatedly complained to deaf ears. On April 23, 1982, Mayor Dennis Wardlow and the City Council declared the independence of Key West. Calling the newly created country the Conch Republic. However, after one minute of seccession, the Mayor (newly Prime Minister) surrendered to an officer of the KW Naval Air Station (NAS) and requested one billion US dollars in “foreign aid.” The roadblocks were removed and Key West has marketed Conch Republic merchandise since.
Mallory Square
This plaza located in Key West is home to the world-famous nightly sunset festival. Appreciate the gorgeous sunsets of the Keys with hundreds of your friends and carnival-like performances with a cocktail in hand.
Duval Street
Undeniably one of the most popular destinations of the Keys is Duval Street. Live music, galleries, coffee shops, and bars lots of bars line the street. Making it the perfect place to roam and bar crawl.
Note: Sloppy Joe’s is famous, but the original Sloppy Joe’s visited by Ernest Hemingway is now the famous Captain Tony’s.
Harry S Truman’s Little White House
Originally waterfront and the first officer’s quarters on the U.S. Naval Station. The house was designed in 1889 by local architectural firm Scott, McDermott & Higgs. In 1911, the building was converted to a single-family home for the base commander and additional land was filled in front of the house.
The home has long been home to American historical leaders. William Howard Taft was the first President to visit in 1912 after a trip on the Overseas Railway. During World War I, Thomas Edison called it home while donating his services to the war effort. Edison perfected 41 underwater weapons during his six-month stay.
In November 1946 after 19 months in office, Truman’s doctor ordered a warm vacation to alleviate his exhaustion. Truman arrived in key West stating he would visit when he needed rest. He quickly set a pattern of arriving every November-December and every February-March. Realizing that where the President was, the White House was Turman spent 175 days in the Little White House.
Other Notable Uses of Truman’s Little White House:
- March 11-14, 1948: Under Dwight D Eisenhower the Key West Agreement was hammered out as James Forrestal met with the Joint Chiefs of Staff to create the Department of Defense.
- Dwight D Eisenhower used the island retreat to recuperate from a heart attack.
- November 26, 1962: John F Kennedy inspected the HAWK missile sites and reassured Americans that Key West was safe in spite of the Cuban Missile Crisis.
- February 12, 1974: The building was added to the U.S. Register of Historic Places.
- January 1, 1987: The building was deeded to the state of Florida and became a public museum opening in 1991.
- 1996: Former President Jimmy Carter held a family reunion here.
- April 2001: Secretary of State Colin Powell opened a week of OSCE peace talks between Armenia and Azerbaijan.
- January 2005: Bill and Hilary Clinton rang in the new year.
Fort Zachary Taylor Historic State Park
On the southern edge of Key West sits Fort Taylor. Predating the Civil War this National Historic Monument once housed the largest cache of Civil War armament in the world. The park is the southernmost state park in the continental United States and one of the few places on Key West to find some beach time.
While visiting the park you can walk the arched brick corridors passing cannon and gun ports. On the third weekend of every month, history comes to life as local re-enactors conduct historic demonstrations.
US Coast Guard Cutter INGHAM Maritime Museum
This 327-foot ship from World War II and Vietnam is now a National Historic Landmark and museum. INGHAM served the country from 1936 to 1988 and in 1985 was the most decorated ship in United States Service. The ship was the last American Warship afloat to have sunk a German U-Boat in World War II.
The ship offers one of the best Sunset viewing areas on the island.
Key West Lighthouse and Keeper’s Quarter’s Museum
After the U.S. Navy established a base in 1823, the need for a lighthouse was evident. It was needed to navigate the shallow reef-laden waters off the Florida Keys. The current lighthouse opened in 1848 powered by 15 oil lamps. In a nearly unheard-of placement for the time, the Keeper was a woman.
In 1969, the U.S. Coast Guard decommissioned the lighthouse due to technological advancements. Today you can climb the 88 ending steps to the top for 360-degree views of the city and ocean.
Southernmost Point
No trip to Key West is complete without a photo at the Southernmost Point Buoy. The concrete buoy marks the southernmost point in the continental United States. It was established as a tourist attraction in 1983. You will find the buoy at the corner of South Street and Whitehead Street, but expect long lines unless you hit it early in the morning.
San Carlos Institute
Founded in 1871 by Cuban exiles as an educational, civic, and patriotic center. The building is now a Cuban heritage museum. The center has moved three times and is now located on Duval Street.
The institute played an important role in Cuba’s history. When in 1892 legendary patriot Jose Marti addressed a gathering. He announced a united front would be best to lead the effort for Cuba’s independence.
Key West Historic Seaport
Visit an authentic slice of old Key West at the seaport. Now lined with restaurants and bars the area dates back to the 1700s when the port had safe anchorage and stocks of drinkable water.
East Martello Museum & Gallery
Constructed in 1862 to protect Fort Zachary Taylor from confederate attacks. The tower is located adjacent to the Key West Airport. The museum features an art gallery, Civil War relics, and exhibits about wrecking and cigar manufacturing. As well as, an exhibit called Ghosts of East Martello including the infamous Robert the Doll.
West Martello Tower
Former Civil War fort, now a tropical garden courtesy of the Key West Garden Club. Garden rooms and history are merged into an inspiring tropical oasis.
Key West Shipwreck Museum
Discover the history of Key West’s shipwrecking past with shipwreck artifacts in the recreation of a shipwreck’s warehouse.
Key West Cemetery
Visit the graves of early settlers and view cheeky epitaphs like “I told you I was sick” and “at least I know where he’s sleeping tonight.”
The map at the main entrance will guide you to some of the more interesting plots.
Oldest House Museum & Garden
Located at 322 Duval Street sits the oldest house in South Florida. Built in 1829, the simple wood frame, its cookhouse, and beautiful gardens are opened daily with docents to relay the rich history.
The builder of the oldest house was Richard Cussans. He immigrated from the Bahamas in 1826 in his mid-twenties. The workmanship on the home indicates he may have apprenticed as a ship’s carpenter.
Audubon House & Tropical Gardens
Home to one of the most beautiful tropical gardens in Key West. The home was built by harbor pilot and master wrecker, Captain John Geiger as a family home between 1846 & 1849. Restored and opened as a museum in 1960, the home holds an extensive collection of original lithographs by John James Audubon. Although it is unclear if Audubon ever visited the house. Audubon was in Key West in 1832 and is thought to have visited the gardens here. While in Key West, Audubon is said to have painted more than a dozen new birds for his Birds of America collection during the island visit.
White Street Pier (AIDS Memorial)
Sitting at the entrance to the White Street Pier the memorial of Zimbabwe granite is etched with the names of those who have passed due to AIDS complications. It is a moving tribute as you approach the pier.
Key West Historic Memorial Sculpture Garden
Opened in 1997, the small garden houses 36 bronze busts and biographies of the men and women who had the greatest impact on the Florida Keys. The largest sculpture titled “The Wreckers” highlights the area’s ship scavenging past.
Dry Tortugas & Fort Jefferson National Park
Located about 70 miles off Key West are seven islands straddling the Gulf of Mexico, the Caribbean Sea, and the Atlantic Ocean. Built as a Civil War fortress, Fort Jefferson is accessible only by boat or seaplane. Famous for great snorkeling in its shallow waters with numerous shipwrecks, the fortress is now a National Park. The fortress was where prisoners of war were kept. The most infamous of which was Dr. Samuel Mudd.
Take a Yankee Freedom Ferry ride to the area.
Hemingway House
While many authors have called Key West home, none may be more known than Ernest Hemingway. The author fell in love with the island where his father-in-law purchased the home as a wedding gift. Now a historic landmark, you can tour. Noted as the first home in Key West to have indoor plumbing and a pool. Hemingway finished A Farewell to Arms just three weeks after arriving in Key West. He later wrote For Whom the Bell Tolls, Death in the Afternoon, The Green Hills of Africa, and several short stories including The Snows of Kilimanjaro here.
Yes, you will see descendants of his six-toed cats too!
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Disclosure: Some links on our site are affiliate links. If you purchase a linked item, we will make a commission, at no extra charge to you.