Florida East Coast Railroad. The "Havana Special."

The extension of rail service to Miami in 1896 transformed the area from a sleepy tropical oasis into a thriving metropolis. All along the route of his railway, Flagler built elegant hotels that would entice tourists to travel on his railroad and then stay as guests at the resorts located just steps from the station.

From the Ponce de Leon and the Alcazar in St. Augustine to the Royal Poinciana in Palm Beach, Flagler’s hotels developed a reputation for featuring some of the most luxurious amenities travelers could expect. Writer Henry James once referred to the scene at the Royal Poinciana as “Vanity Fair in full blast.” The same was true for the Royal Palm Hotel, opened in Miami just one year after the railroad line was completed there. Yet Flagler wanted a deep-water port as the terminus for his railway.

Beginning in 1905, construction began on the Key West extension of the Florida East Coast Railway, which would become known as the “railway that went to sea.” The line was completed in 1912 and comprised seventeen miles of bridges and twenty miles of embankments linking the Keys together from Homestead to Key West. The “Havana Special” was a deluxe passenger car  that took travelers all the way from New York to Key West in record time (supposedly four hours, though most often longer) so they could then depart on a ferry for Havana. The train ran until 1931, when the line went into receivership. Following a devastating hurricane in Islamorada in 1935, much of the trackbed was washed away. The remains of the railway were used to construct the new Overseas Highway, completed in 1938.