Skip to content
open search box
Old Town Trolley Old Town Trolley Tours St. Augustine sightseeing tours
St. Augustine tours


View of St. Augustine from Matanzas River

The History of St. Augustine

Over the past 450 years, St. Augustine has grown from a fledgling European settlement and military outpost ridden with violence and turmoil to Henry Flagler’s Gilded Age in the late 1800s. Today, the historic city lays claim to one of Florida’s up-and-coming cultural hubs with a vibrant art and music scene.

Let’s take a walk through the ages and explore St. Augustine’s storied past riddled with privateers and plunderers, innovators and inventors, the rich, the royal and those just looking to make the city a better place to live.

Settling Down

Florida had several unsuccessful settlement attempts in the 1500s; but they did not stick until conquistador Pedro Menendez came to St. Augustine in 1565 and launched a period of Spanish rule. This was 42 years before the English colonized Jamestown and 55 years before the Pilgrims landed at Plymouth Rock.

Transforming with the Times

The oldest continuously occupied settlement of European and African-American origin in the United States, St. Augustine has undergone numerous transformations. The city served as the capital of Spanish Florida for over 200 years and remained the capital of East Florida when territory briefly changed hands between Spain and Britain. In the early 1800s, the Sunshine State was ceded to the United States by Spain.

An Oasis for the Elite

In the 1880s, with Henry Flagler, an American industrialist and railroad magnate, St. Augustine became a winter resort for the wealthy northern elite. The city maintained this prestigious status and extravagance for decades until the Great Depression and World War II ravaged the country.

Historic Importance

Fast-forward to the 1960s when the Nation’s Oldest City became a pivotal site of the Civil Rights Movement. From marches, sit-ins and other forms of peaceful protest, St. Augustine made a name for itself as a progressive locale to help spur tolerance and a change in mindset evident today.

The city was also the setting for Martin Luther King Jr.’s 1963 arrest for protesting the segregation at Monson Motor Lodge, which has since been demolished.

A Must-See Destination

Considered the modern era, St. Augustine has become one of the top tourist destinations in the Southeastern United States complete with boutiques, attractions, eateries and plenty of history. The city is consistently ranked among the best cities in the South and has become a hot spot for art, live music, outdoor sport, historical sites and themed attractions.

Up Up
Back to top