The term "Five Flags" is most famously associated with Pensacola, Florida, which is known as "The City of Five Flags." The name refers to the five different governments that have held sovereignty over the city since its first European settlement in 1559. These nations are Spain, France, Great Britain, the Confederate States of America, and the United States. Pensacola has a complex colonial history: it was first settled by the Spanish, captured by the French in 1719, handed to the British in 1763 after the Seven Years' War, retaken by Spain in 1781, and finally ceded to the U.S. in 1821. During the American Civil War, it was briefly under the Confederate flag before being recaptured by Union forces. In 2026, the city celebrates this multicultural heritage through various historical sites and the "Fiesta of Five Flags," an annual festival that honors the unique blend of Spanish, French, and British influences that still define the region's architecture and culture.