How to Spend 2 Days in St. Augustine with Kids

St. Augustine, Florida, is the oldest continuously occupied European settlement in the United States, with a history stretching back over 450 years. Founded by Spanish explorer Pedro Menéndez de Avilés on September 8, 1565, St. Augustine was established as a strategic military outpost and colonial settlement, securing Spain’s claim to the Florida territory.

Long before European arrival, the region was home to the Timucua people, who had lived along Florida’s northeastern coast for thousands of years. When the Spanish landed, they encountered these Indigenous groups, engaging in both cooperation and conflict.

Over the centuries, St. Augustine was the focal point of power struggles between Spain, France, Britain, and later, the United States. The city endured pirate raids, attacks from British forces—including those led by Sir Francis Drake in 1586—and shifts in colonial rule. It remained under Spanish control until 1763, when it was ceded to Britain, only to be returned to Spain in 1783. In 1821, Florida became a U.S. territory, and St. Augustine became a key center of American expansion.

During the 19th century, St. Augustine evolved into a resort destination, largely due to the efforts of Henry Flagler, an industrialist who built grand hotels and expanded the Florida East Coast Railway, transforming the city into a hub for tourism.

In the 20th century, St. Augustine played a significant role in the Civil Rights Movement. In 1964, activists led protests against segregation, drawing national attention and influencing the passage of the Civil Rights Act of 1964.

Today, St. Augustine is celebrated for its rich colonial heritage, cobblestone streets, Spanish architecture, and historic landmarks such as Castillo de San Marcos, the Fountain of Youth, and Flagler College. Its unique blend of Spanish, British, and American influences makes it a living museum of the past, drawing visitors from around the world.