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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.

Discover the magic of wintertime in St. Augustine and embark on a historical “Transportainment®” adventure!

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.

Chief Saturiwa statueSettling Down

Long before any influence or incursion arrived from Europe, thousands of years by most accounts, there lived an indigenous population known as the Timucua Indians in the land we know today as St. Augustine. The little that is known of these people is largely found in historical European documents and unearthed archeological artifacts that give us an understanding of how they lived. For example, these records show that the Timucua lived in circular, thatched-roof homes in highly organized communities where the chief was often a woman.

When Spanish explorer Pedro Menendez arrived in 1565 to eventually settle this land in the name of the Spanish crown, they were welcomed with open arms by the Timucua, who generously offered their homes and village to the hundreds of men that landed on their shores. This collision of Old and New worlds was the first time in recorded history that Indian and Spanish populations co-habitated for the many months they subsequently did. This living arrangement has been recreated in what is today the Fountain of Youth Park, so visitors may learn what life in the fledgling settlement was like over 450 years ago.

Eventually, however, hostilities arose between the groups which resulted in a steady decimation of the indigenous population, mostly due to disease brought there by the Spanish. Two hundred years after Menendez’s landing, Spain ceded Florida to Great Britain and the Spanish evacuated to Cuba with the remaining 100 or so Timucua.

Transforming with the Times

The oldest continuously occupied settlement of European and African-American origin in the United States, St. Augustine underwent numerous transformations over the centuries. During their initial reign, the Spanish, in addition to claiming land for strategic military purposes, sought to import Catholicism to this distant land by enlisting hundreds of Franciscan priests to start missions among the indigenous people that stretched as far west as Pensacola and north to the Carolinas. For the duration that the Spanish attempted to establish their foothold on St. Augustine, conflict with Great Britain came early and often. Soon after the advent of the Anglo-Spanish War in 1586, a large British fleet, led by privateer Sir Francis Drake, overwhelmed the Spanish forces in St. Augustine and the settlement was burned to the ground. In the early 1600s, expeditions were sent from St. Augustine to attack the British colony at Jamestown, Virginia. Displaced Indians from the north attacked the missionaries in St. Augustine during the second half of the 17th century. And in 1668, St. Augustine was sacked again by British buccaneers which prompted the building of a permanent masonry fort which, today, is one of St. Augustine’s most iconic landmarks – the Castillo de San Marcos. After more years of strife that saw St. Augustine razed yet again by the British, Florida was finally ceded by the Spanish in 1763 to their enemy for what was a brief 20-year period before the Spanish eventually returned to reclaim the land. But not for long…

An Oasis for the Elite

While a revolution swept South America and Napoleon’s armies threatened to conquer Europe, it became harder and harder for the Spanish to protect its global interests. Florida, during this tumultuous time in history, was not a priority for the Spanish crown which was spread too thin and depleted of resources. The United States, a young, ambitious nation fresh off its own revolution, was expanding and coveted Florida as an ideal territory to bolster their military interests. In 1821, the United States swooped in and acquired the land from Spain via treaty and it’s been in American hands ever since.

The rest of the 19th century consisted of wars with the local Seminole, Creek and Miccosukee peoples in a struggle for land, a huge spike in population growth by white settlers, and a fleeing of the population when the Union Army reclaimed St. Augustine from Confederate control in 1862. It wasn’t long, however, before a certain wealthy industrialist would train his eye on St. Augustine and usher in a new era of prosperity that would make him a legend. Henry Flagler, a man who made his fortune in the oil business, sought the warmer climes of St. Augustine as a respite for his ailing wife. He immediately saw massive potential in this small town as a vacation hotspot for wealthy northerners and proceeded to invest heavily in St. Augustine’s infrastructure. Ornate hotels began to spring up built in the Spanish and Moorish Revival styles completely altering the skyline. His most important contribution, however, was the building of the Florida East Coast Railway that initially extended from Jacksonville to the north to St. Augustine with its terminus eventually reaching hundreds of miles south to Key West. Flagler’s ambitious project to revitalize the ‘Ancient City’ was a game-changer that resonates today having transformed St. Augustine into a major player of the Florida tourism industry.

Fort San MarcosThe 20TH Century & Beyond

With the United States entering the Second World War in retaliation for the Japanese attack on Pearl Harbor, Americans quickly had to adapt to a wartime economy that saw the entire nation tighten its belt for the war effort, including the citizens of St. Augustine. Because of the rationing of all resources, and in St. Augustine’s case the scarcity of gasoline, the tourism industry was effectively held to a stand still. This was a massive blow to the local economy until it slowly started to recover over the next several years thanks to thousands of Coast Guard servicemen being sent to the city for training.

After the war ended, the city began to prosper again through the 1950s with the building of new museums, the filming of a movie starring silver screen legend Gary Cooper, and the rolling out of sightseeing trains that remain a staple of St. Augustine to this very day.

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.

Throughout the 1990s there was a push, spearheaded by the Historic St. Augustine Preservation Board, to restore over 36 buildings to their original condition. In 2010, the board’s control was transferred to a support organization affiliated with the University of Florida which currently oversees the city’s historic preservation, archaeology, cultural resources management, cultural tourism, history, and museum administration.

In 2015, St. Augustine celebrated the 450th anniversary of its founding with a four-day long festival and a visit from Felipe VI and Queen Letizia of Spain.

How To See It All

Get MORE out of your summer in St. Augustine aboard the iconic Old Town Trolley and see the best first!

You say you can’t pack in over 450 years of history into a 90-minute tour?? Think again!

For many years, Old Town Trolley Tours has been the voice of St. Augustine, providing the finest, safest, most comprehensive tour of the city. All the tours are guided and narrated by experts who know the ‘Ancient City’ inside and out with equal parts information and entertainment. Not only will you experience the absolute best tour of St. Augustine by the people who know it and love it most, you’ll have the flexibility to do it at your own pace! The hop-off hop-on feature of the tour allows you to board and disembark at any of their stops at any time during operating hours which means more time walking St. George Street, browsing the Lightner Museum, marveling at the Castillo de San Marcos, or taking a sip of rejuvenating water from the magical well at the Fountain of Youth!

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 sports, historical sites and themed attractions.

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