Florida seceded during the Civil War, but naval presence kept Key West under Union rule throughout the conflict. Afterwards, fishing resumed. Immigrants flooded in from the Bahamas. And from Cuba. The Cubans staffed cigar factories, key to the next boom economy.
Our guide Jennea pointed out examples of local architecture. Shotgun cottages were built by cigar factory owners for their workers. An occasional ornate Victorian survived the city's worst fire in 1886. Tin roofs, required after the fire, also facilitated collection of water in cisterns.
Vernacular construction mixed New England and Bahamian influences, including exterior shutters, wraparound porches, lots of gingerbread and eyebrow windows designed to assist ventilation (which they didn't). An occasional ship captain's home is capped by a widow's walk.
The now dormant Flagler Station provided a chance to describe the next major event. Henry Flagler, once a partner of John D. Rockefeller in Standard Oil, had built railroads down the east coast of Florida. He opened grand hotels along the way to lure tourists to the region. His most audacious project was to build tracks from Miami all the way to Key West, a 130-mile route that crossed almost as much water as land. Virtually everyone in town turned out to greet the first arriving train in 1912. That, plus completion of the Panama Canal, helped Key West thrive as a port.
World War I and the Great Depression devastated the economy. Beautification projects and grand tourism plans sought to recapture Key West's halcyon days. The hurricane of 1935 quashed that initiative when it roared through, destroying the rail line and killing several hundred people on the Keys.
Cigar manufacturing is long gone. So is commercial fishing, though as recently as the 1950s, more than 300 shrimp boats operated from the harbor. The rail route never got rebuilt. It was replaced instead by the Overseas Highway, itself an engineering marvel, along the same route that Flagler brought trains.
Tourism has come back, of course, and appears to be stronger than ever.
Duval Street recalls a mix of vintage Lake George and Gatlinburg, with perhaps a bit of New Orleans and Havana mixed in. Every bar — and there are plenty — offers some kind of legend. Maybe Ernest Hemingway or Tennessee Williams had a drink here. Or Jimmy Buffett performed there. You get the picture.
At one corner stands the southern terminus of US Route 1 (2,209 miles to Fort Kent, Maine). Near another is a building that housed the first office of Pan American Airways. Its first route, in 1926, was Key West to Havana. Somewhere else, a monument marks the southernmost point of the United States. No sign marks the highest elevation on the island, an awe-inspiring 18 feet.