Key West, Florida
When people have noted — as John F. Kennedy did during the Cuban Missile Crisis — that communist Cuba lies only 90 miles off the U.S. coast, they are actually referring to Key West. This island and city of some 26,000 people is often called the southernmost city in the United States, near the end of the long, jagged line of Florida Keys extending from the tip of the state in a hook that reaches west toward the Gulf of Mexico.
This territory has always had a curious, liminal place in U.S. history. Supposedly, the island was serving as a burial ground for the indigenous Calusa people when it was first visited by Spanish explorers in the 16th century. Throughout the 18th and 19th century, the island changed back and forth between Spanish and British hands along with the rest of Florida, until the United States made its definitive and uncontested claim in 1822. Prior to this and until 1912, Key West was relatively isolated from the mainland, with no reliable overland routes to Miami, itself a small settlement until the 20th century and about 130 miles away.
Initially, Key West attracted U.S. development as a strategic naval location situated between the Atlantic Ocean and the Gulf of Mexico, and the city and the surrounding islands still host major naval bases. Due to this military presence, Key West remained in Union hands throughout the Civil War, even as many residents openly expressed sympathies with the rest of secessionist Florida.
However, Key West has had a stint as a secessionist enclave from the United States. When Fidel Castro briefly permitted Cuban citizens to leave at will during the Mariel boatlift of 1980, immigrants flooded south Florida. In an effort to control the influx, U.S. Border Patrol agents blockaded the Florida Keys and set up a roadblock akin to an international border checkpoint. Due to the inconveniences caused to Key West residents and tourists, the mayor and city council declared independence as the “Conch Republic,” which uses the name for the Bahamian immigrants who formed the bulk of the island’s original immigrant population. The birth of the Conch Republic is still celebrated every year on the April 23rd “Independence Day,” with a week of celebrations showcasing the community’s quirky, laid-back sense of humor.
Key West’s beauty, temperate weather, and colorful culture has attracted exceptional residents. Ernest Hemingway had a home in Key West, where he lived and wrote during the 1920s and 1930s before decamping for Havana. Tennessee Williams, too, lived and worked there beginning in the 1940s. Presidents Taft, Franklin D. Roosevelt, Truman, Eisenhower, Kennedy, and Carter all spent varying amounts of time in Key West, but only Truman kept a dedicated residence, his “winter White House,” there. The Truman Annex has now been divided between a naval base and residential properties, but Truman’s “Little White House” remains open to visitors. The property still occasionally attracts extended visits from important visitors on both official and recreational visits, including Colin Powell and the Clintons.
Today, Key West is frequently visited by cruise ships. The island’s population balloons as tourists head into town to wander its narrow, sunbaked streets, explore its various historical and recreational attractions, and soak up the Caribbean atmosphere.