This is, quite literally, the end of the road. Leaving the southern tip of the Floridian Peninsula, drivers hop from island to island, covering a total of 113 miles over 42 bridges. Yes, it’s touristy—a very popular destination for Americans and international travelers alike.
But the locals will tell you, and it’s true: The Conch Republic feels like a world apart.
On this day, I arrived by ship. First, from the top deck, I took in the view of this lovely city, whose splash and dazzle are so different than any other place in the United States. It has flashing aquamarine water, swaying green palms, and streets lined with buildings painted every color of the rainbow.
And then I descended onto shaded streets, sylvan, quiet, and lovely.
A rooster strutted past me, like he owned the street. (More on the free-roaming fowl, later.) Ahead, in the span of a few blocks, I was about to find a wealth of history and culture. One day wasn’t enough to discover Key West—but it was going to be an excellent day, nonetheless.
America’s Farthest Shores
Cities at the end of the road tend to be interesting places, largely because of the people who choose to settle there. They are often wanderers and creative types, with nowhere left to drive, so they lay down roots. And, sitting out there in the Gulf of Mexico, the southernmost point in the United States, Key West is the ultimate version of an end-of-the-road town. Once, they even declared themselves an independent republic.
The island—just four miles long and one mile wide—was first deeded by the Spanish governor in Havana to an artillery officer in 1815. He, in turn, sold the land to an Alabama businessman for $2,000. In 1822, the USS Shark landed here. The American flag was planted, and Key West became part of the United States.
The island was considered by some to be the Gibraltar of the West, and Fort Zachary Taylor, completed in 1866, played an important role in the Civil War. In the second half of the 19th century, life lurched along with income from salt manufacturing, fishing, and other maritime industries.
But things really got going in the first half of the 20th century. Henry Flagler connected the island to the mainland with his famous railway, which, after it was destroyed in the Labor Day Hurricane of 1935, was transformed into the Overseas Highway. An extension of famous US Highway 1, President Franklin Roosevelt drove the route in 1939.
In the following decades, some of Key West’s most famous residents started to arrive here at the end of the road. As I made my way toward Duval Street, the sounds of live music were already in the air, despite the fact that it was currently midday on a weekday. I passed not one but two bars claiming to be Ernest Hemingway’s favorite drinking hole. The famous Sloppy Joe’s Bar was in its prominent corner location. But there was also a place called Captain Tony’s Saloon, whose sign says it’s the oldest bar in Florida and the original Sloppy Joe’s.
On the Waterfront
I duck into a couple of pubs on Duval and enjoy the music, mostly one-guitar acts singing catchy covers of popular songs. At the Key West Historic Seaport harborwalk, I strolled the boardwalk, watching the busy marina bustle of fishing charters and snorkel boats leaving and coming back from the Gulf of Mexico.
I sat for a moment and enjoyed the water-borne spectacle as three hens clucked by my feet. I asked around about these thousands of roosters, chickens, and chicks that wander the island. I was told that, in days past, when Key West was totally cut off from the rest of the country, people kept them in pens for food in their backyards.
Additional birds were brought from Cuba for cockfighting. But as time marched forward and supermarkets opened, people quietly set them free, or they escaped, sometimes after hurricanes blew apart their pens. Despite a couple of notable attempts to round them up, these birds continue to rule not just the roost, but indeed the whole island. Some people have observed they share a few traits with local residents—loud and a little wild.
Looking up, I spotted the bright, cheerful flag for the Conch Republic, which remains ubiquitous here. In a publicity stunt that worked spectacularly well, the mayor of Key West declared the island an independent micro-nation on April 23, 1982. The locals had long called themselves Conchs, and they declared war, but surrendered just one minute later. Every year in April, Key West still celebrates Independence Day.
The Presidents’ House
Making my way back to the ship, I spent a little time at the Truman Little White House Museum. On a previous visit, I’d done a full tour, but with all-aboard on the ship soon, today I had only a little time to walk the grounds and chat with a couple of the guides.
The two-story wooden building was completed by the U.S. Navy in 1890 and went on to house many famous residents. President William Taft and Thomas Edison spent nights here, as did FDR. Both Presidents Dwight Eisenhower and John F. Kennedy held important meetings in this pretty house near the water. But it was Harry S. Truman who used it the most, residing here over the course of 11 working vacations that totaled 175 days.
The grounds are lush, filled with date and coconut palms and mango and avocado trees. A guide told me about the presidential limousine that sits on the grounds, one of Truman’s fleet. He also showed me a famous black-and-white photo of Truman, then an under-the-radar vice president, playing piano with a leggy, at-the-time-unknown actress named Lauren Bacall draped across the back of the grand piano.
“Everybody loved this photo,” the guide told me, everyone, that is, except Truman’s wife, Bess. He added that it became a national scandal.
“He never played piano in public again,” the guide laughed.
Making my way back to the ship, I marveled at how one small island can be filled with so many stories. Every block, it seemed, had a tall tale to tell.
