Key West International

Ernest Hemingway bought the Spanish Colonial house at 907 Whitehead Street in Key West in 1931 for $8,000 — his second wife Pauline's uncle put up the money. Over the next decade he wrote some of his best-known work there: "To Have and Have Not," "Death in the Afternoon," "The Snows of Kilimanjaro," much of "For Whom the Bell Tolls," and the Esquire dispatches that bankrolled the lifestyle. He left in 1939 for Cuba, but Pauline and the house stayed. The house is the second-oldest in Key West, built in 1851 by marine architect Asa Tift in the French Colonial style with a wide veranda and an iron filigree balcony. The in-ground pool — the first in Key West, built by Pauline in 1938 while Hemingway was reporting from Spain — cost $20,000, more than twice what he paid for the house. He reportedly pressed a penny into the wet cement and said she had taken his last cent. The penny is still there. Hemingway's six-toed cats (polydactyl, a genetic trait) are the house's other legend. A sea captain named Stanley Dexter gave him a polydactyl cat named Snow White; the descendants — about 60 cats, half of them six-toed — still roam the property. They are named after famous people: Audrey Hepburn, Marilyn Monroe, Ernest Hemingway himself. A few blocks away, Old Town Key West concentrates two centuries of history into ten walkable blocks. Mallory Square at the harbor hosts the nightly sunset celebration — buskers, fire-eaters, cat-show acts, tourists drinking from plastic cups. Duval Street runs the length of Old Town, from the Gulf side to the Atlantic side; "Mile Marker 0" of US-1 is at the corner of Whitehead and Fleming, four blocks north of Hemingway's house. The Southernmost Point monument (concrete buoy painted in stripes) sits at South Street, 90 miles from Cuba.

Henry Flagler — Standard Oil partner, Florida's railroad baron — decided in 1905 to extend his Florida East Coast Railway from the mainland all the way to Key West. He was 75 years old, going blind, and the engineers told him the project would take a generation. He pushed it to completion in seven years anyway. Contemporaries called it the Eighth Wonder of the World. The Seven Mile Bridge between Knight's Key (now part of Marathon) and Little Duck Key was the project's longest single span — 35,716 feet of trestles, swing spans, and arched piers across open ocean. At the height of construction (1908-1912), 400 men lived on five-acre Pigeon Key, the tiny island under the bridge that served as a construction camp. They worked 12-hour shifts, 24 hours a day, $1.50 a day. Two work shifts of 12 hours each meant the bridge was being built around the clock — and that work pattern is supposedly how the town of Marathon got its name. Flagler insisted on no alcohol in his camps; the deck plate connecting Pigeon Key to the mainland was deliberately laid last, to keep his men dry. The railroad was completed on January 22, 1912. Flagler, blind from cataracts, rode the inaugural train down to Key West. He died sixteen months later. The Over-Sea Railroad operated for 23 years until the Labor Day Hurricane (Category 5, September 2, 1935) wiped out 40 miles of track and killed an estimated 423 people. The Florida East Coast Railway didn't have the money to rebuild and sold the right-of-way to the state. By 1938 the bridges had been converted to carry the Overseas Highway. A new, wider Seven Mile Bridge opened in 1982 — straighter, higher, two lanes plus shoulders. The original was kept as a pedestrian and bike pier, closed in 2017 for a $43 million restoration, and reopened January 12, 2022. The reopened 2.2-mile section connects Marathon to Pigeon Key, which is now a National Register Historic District with the original 1908-era worker buildings preserved as a museum. Visitors walk, bike, or take a small tram to reach the island. Movie credits: True Lies (1994), License to Kill (1989).

The Overseas Highway (US 1) stretches 113 miles from Key Largo to Key West across 42 bridges, including the iconic Seven Mile Bridge. From the air, the thin ribbon of concrete over turquoise water is one of the most visually stunning pieces of infrastructure on Earth. The water color shifts from deep blue to brilliant turquoise to jade green depending on depth. Fly it at 1500ft southbound for maximum drama.

70 miles west of Key West — the most remote unit in the National Park system. Fort Jefferson, an unfinished hexagonal masonry fort begun in 1846, holds 16 million bricks and was meant to control Gulf of Mexico shipping. Dr. Samuel Mudd was imprisoned here after treating John Wilkes Booth's broken leg. Today reachable only by boat or seaplane. Crystal clear water for snorkeling, the largest tern rookery in the western hemisphere, and a fort that feels like the end of the world.