Florida Keys: Hemingway, Truman & the History Beneath the Water

The first underwater state park in the United States — established in 1963 to protect a 25-mile stretch of living coral reef off Key Largo. Named for Miami Herald editor John D. Pennekamp, whose conservation advocacy drove the park's creation. The visitor center has a 30,000-gallon reef aquarium and exhibits on reef ecology. Glass-bottom boat tours depart throughout the morning for the reef; the famous submerged Christ of the Deep statue (a bronze Jesus with arms raised, placed on the seafloor in 1965) is visible without snorkeling on the glass-bottom tour.

The most comprehensive museum of diving history in the world — 4,000 artifacts, 13 diving bells, and equipment spanning 4,000 years of human underwater exploration, from ancient Greek sponge divers' tools to Cold War Navy deep-sea suits. Founded in 2005 in Islamorada by divers Sally and Joe Bauer, the museum traces how humans have descended beneath the surface, with fully restored hard-hat suits, rebreathers from the 1940s, and the only publicly displayed Neufeldt-Kuhnke atmospheric diving suit in the Western Hemisphere.

One of the oldest marine mammal parks in the world — opened in 1946 in a series of natural saltwater lagoons carved when Flagler's railroad dredged the island fill. Theater of the Sea holds bottlenose dolphins, Atlantic sea lions, sea turtles, and tropical fish in interconnected lagoons rather than tanks, making it a more naturalistic setting than most marine parks. The dolphin swim programs and sea lion shows are the main draws; the saltwater lagoon environment is the differentiator.

Islamorada's landmark resort — 27 acres on the Atlantic side of Upper Matecumbe Key, with a fishing pier extending into the Atlantic, six restaurants and bars, and a 1,100-foot beach. Cheeca Lodge has hosted presidents and celebrity anglers since the 1940s and remains the Upper Keys' most established full-service property. Tomorrow's drive to Key West starts early — the 2.5-hour run on US-1 through the Lower Keys is best done before noon.

The 1851 Spanish Colonial mansion at 907 Whitehead Street where Hemingway lived from 1931 to 1939 — during which he wrote A Farewell to Arms, To Have and Have Not, The Snows of Kilimanjaro, and For Whom the Bell Tolls. The first house in Key West to have a swimming pool (which Hemingway's wife Pauline had dug, allegedly costing so much that he threw his last penny into the concrete). About 40-50 polydactyl (six-toed) cats descended from Hemingway's original cat roam the grounds.

The only authentic presidential museum in Florida — the 1890 Commander's Quarters at the Key West Naval Station where Harry Truman stayed 11 times for 175 days total, making it his preferred working retreat. Nine other presidents used the building, including Eisenhower, Kennedy, and Carter. The house is fully restored with original Truman-era furnishings, and the guided tour (the only way to enter) covers not just Truman but the building's role as a secondary seat of Cold War-era decision-making.

The Key West Cemetery — 20 acres in the center of the island, established after an 1846 hurricane washed the original cemetery off the beach — holds 100,000 interments in a city of 25,000 living people. Above-ground tombs are used throughout due to the island's shallow limestone bedrock. The cemetery is known for its witty epitaphs: 'I told you I was sick,' 'Devoted fan of Julio Iglesias,' and a section dedicated to the victims of the USS Maine. The adjacent Old Town streets — Duval, Petronia, and Emma — are the best Key West architecture walk.

The tallest building in Key West and one of its oldest hotels — a 1920s seven-story landmark on Duval Street, now an Autograph Collection property. The rooftop observation deck gives the only elevated view of the island and the Gulf; Hemingway used it as his model for the fictional Hotel Perla in To Have and Have Not.

A Union-held Civil War fort on the western tip of Key West — built between 1845 and 1866 in a hexagonal plan using 5 million bricks, and one of the most intact Civil War-era forts in the US. Fort Taylor never fell to Confederate forces and played a critical role in the Union blockade of Confederate ports. The fort was buried under fill for decades after the war; archaeologists in the 1970s excavated the largest collection of Civil War cannons ever recovered in a single location. The park also has the best beach on Key West — on the Gulf side, with calmer water and less seaweed than the Atlantic beaches.

The 1848 Key West Lighthouse — 88 steps to the top of the 86-foot tower, with panoramic views across the island, the Gulf, and the Atlantic in all directions. The lighthouse keeper's quarters below have been restored to their 1890s appearance and interpret the lives of the lighthouse families who maintained the light. The museum is operated by the Key West Art & Historical Society, which also runs the Custom House museum nearby.

Mallory Square is Key West's harborside gathering point — famous for the nightly sunset celebration, but at midday a quieter place to look out at the Gulf and the commercial fishing harbor. The Custom House behind the square is an 1891 Richardsonian Romanesque building that processed all of Key West's wrecker and shipping revenue at a time when Key West was the wealthiest city in Florida (the wrecking industry — salvaging cargo from ships run aground on the reef — made it so). The building now houses a comprehensive Key West history museum.