Early Key West was a rugged place, home to grim shipwreck lifeguards, salt miners, and US military personnel manning the island’s strategically critical fortress. Many 19th century structures, and countless stories, survive in Old Town Key West, the historic district on the western half of the island of Key West. Other parts of the Keys also have some surviving historical points of interest.
Mallory Square
Located near the “top” (northernmost end) of Duval Street, Mallory Square is a lively collection of shops, restaurants and outdoor vendors set in a historic setting. In the late afternoon, the area comes alive with street performers, street vendors, and curious homeless people. Be warned: with so many memorabilia on display, it’s very easy to part with your money here.
Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum, or Hemingway House, is a stately former mansion on Whitehead Street in Old Town. Built by a shipping magnate in 1851, the house was purchased by Hemingway and his second wife Pauline in 1931. The Hemingways undertook a massive renovation and expansion that included the addition of an inground pool (then the only such pool in Key West). at a staggering cost of $20,000.
Cat lovers take note: The property is home to more than 50 cats descended from Hemingway’s six-fingered cat, with about half sharing the unusual morphology of his ancestor.
Harry S. Truman Little White House
A Missourian with no real ties to Florida, President Harry S. Truman loved Key West nonetheless. Who can blame him? The 33rd president of the US visited the island a total of 11 times, using the Little White House (originally a naval post) as his winter home away from home.
Today, the building is owned by the State of Florida and is managed by a non-profit institution, which maintains its historical artifacts in good condition and provides interpretive content.
Audubon House y Tropical Gardens
Built by a wealthy sea captain in the 1840s, the Audubon House is one of the oldest structures in Key West. It remains in excellent condition, its interior a tour de force of 19th century furniture and art. Audubon House also has a robust bank of interpretive content about the shipwreck salvage industry that Key West built, in part.
Outside, the manicured tropical gardens contain more than 200 orchids and a colony of beautiful, delicate butterflies.
Henry Flagler Overseas Railway
As you drive along Overseas Highway in the Middle and Lower Keys, particularly near Bahia Honda State Park and the Seven Mile Bridge, you’ll likely notice segments of old, decrepit railroad bridges that parallel the highway.
That’s what’s left of an old route that railroad magnate Henry Flagler (who contributed more than any other individual to the growth of South Florida in the early 20th century) built from Miami to the Lower Keys, formally known as the Key Extension. Florida’s West East Coast Railroad, or simply, the Overseas Railroad.
Fort Zachary Taylor Historical Historical Park
Fort Zachary Taylor Historic State Park occupies the westernmost part of Key West. It includes a well-kept old fort that played a critical role (and remained in Union hands, unlike the rest of Florida) during the Civil War, as well as extensive natural areas and a natural-sand beach that’s perfect for swimming and snorkeling.
Dolphin Research Center
Located on Grassy Key, halfway up the Keys, Dolphin Research Center is a facility open to the public that houses dolphins and sea lions in human environments. It is open all year, although the hours and programming may vary according to the needs of the animals.
