Why Pensacola is known as the ‘City of Five Flags’

Plaza De Luna Memorial Monument in downtown Pensacola, honoring Spanish explorer Don Tristán de Luna, who first settled Pensacola in 1559. [Photo by Pensacola Press]

With its sugar-white beaches, emerald Gulf waters and deep naval roots, Pensacola is one of Florida’s most picturesque and historically rich cities. But beyond its scenic charm and seaside hospitality lies a nickname that tells a complex tale of colonial conquests, shifting sovereignties and resilient cultural identity: the “City of Five Flags.”

This title refers to the five governments that have flown their flags over Pensacola since its establishment in the 16th century. Few cities in the United States have such a diverse political history, which has helped shape Pensacola’s identity.

The story begins in 1559 when Spanish explorer Don Tristán de Luna led the first European settlement in what would become the continental United States. Though this initial settlement was short-lived because of hurricanes and hardships, it marked the beginning of Spanish claims over the region. Spain would return and maintain influence for nearly 200 years, from 1698 until the early 19th century. The Spanish legacy is visible in Pensacola’s architecture, street names and traditions.

In 1719, during the War of the Quadruple Alliance, the French took control of Pensacola, the city’s second flag. Their rule was brief, only about a year, but left a mark on the cultural mosaic of the city through French names and culinary traditions.

After the Treaty of Paris in 1763, Britain gained control of Pensacola, which became the capital of British West Florida. The British flag flew over Pensacola for two decades, during which the city experienced growth as a trading and military outpost. The British introduced Protestant religious institutions and new legal frameworks, laying foundational elements for Pensacola’s future governance.

After Britain’s defeat in the American Revolution, Spain in 1781 regained control of West Florida, including Pensacola, and held it until 1821. Pensacola had become a strategic colonial city with a diverse population that included Native Americans, Africans, Europeans and mixed-race settlers.

In 1821, Spain ceded Florida to the United States, the fourth and current flag in the city’s five-flag history. Pensacola became part of the U.S. territory of Florida, which was admitted as the 27th state in the Union in 1845.

The Confederate “Stars and Bars” was the fifth national flag, flying over Pensacola from 1861 until the Union captured the city in May 1862 and restored the U.S. flag.

Today, Pensacola celebrates its multicultural roots and historical resilience. The “Five Flags” theme is evident in everything from festivals and tourism branding to the names of businesses, streets and even the city’s Five Flags Speedway.