Carriage Barn

Built as an auxiliary building, this carriage house was designed as a horse and mule stall. Structures like this were often used to house cows and a wide range of livestock in the crowded and congested neighborhoods of Key West's Historic District. This structure has stayed true to its original architectural style with shiplap siding, a metal clad roof, and sliding barn doors. These buildings predate the use of automobiles and were an integral part of local transportation in the 1800s.

Truman's Little White House

While this house was built for the commanding officer of the Key West Submarine Base, its use by President Harry S. Truman as a site for working vacations earned it fame as "The Little White House." During Truman's 11 trips here from 1946-1953, he negotiated policies ranging from the Marshal Plan and Truman Doctrine, the recognition of Israel, and penning executive orders governing Civil Rights. In subsequent years, the building continued to be used by other presidents for work and leisure.

San Carlos Institute

The San Carlos Institute was founded by Cuban exiles who came to Key West in 1871 to plan the campaign for Cuba's independence from Spain. Many legendary figures of Cuba's independence movement addressed the exile community at the Institute. The most prominent was José Martí, Cuba's legendary patriot and poet. This building, built in 1924, was designed by celebrated Cuban architect Francisco Centurión and served the community as a heritage center and as one of the United States' first integrated bilingual schools.

Schooner Western Union

Built between 1938 and 1939, the Western Union is one of the oldest surviving wooden working schooners in the United States and the oldest remaining built in Key West. It laid and maintained telegraph cables between Key West, Cuba, and the Caribbean Island nations. The ship is the flagship of City of Key West and was named the flagship of the State of Florida in 2012. It was listed on the National Register of Historic Places in 1984.

Norberg Thompson

Norberg Thompson, a self-made man and entrepreneur, owned most of the historic district. During the Great Depression, Thompson employed nearly 40% of Key West's residents. His businesses included ship building, sponging, fishing, canning, ice production, cigar box production, and transportation. He pioneered the local shrimping industry, which expanded during the "Florida Pink Gold Rush" (1949- 1970s). Thompson served as mayor from 1915-1917. He was a man of vision and enterprise, featuring prominently in Key West's early 20th century economic development.