Oldest City in America – St. Augustine’s Fascinating History

The history of the city is dense, often complicated, varied, and even frightening. St. Augustine’s fascinating cultural history carries you through high-end luxury architecture, spooky ghosts, and dastardly pirates. This is what you get with a city over 450 years old, in Florida, on the edge of the water.

Architecture and Development

One of the big pillars of St. Augustine’s history is in the architecture. There are at least two main buildings that are bound to capture your attention. The first is Flagler College, a project developed by business tycoon Henry Flagler, a man largely responsible for turning St. Augustine into a luxury haven for esteemed guests of honor. The second is the Villa Zorayda, the home of a billionaire who sought to stock it with some of the most luxurious and breathtaking Spanish art and decor in the world.

Both of these buildings represent the pinnacle of the city’s last 150 years in décor and design. There’s also the Cathedral Basilica, the Lightner Museum, and the Governor’s House for more architectural history.

War and Conquest

Capturing St. Augustine wasn’t easy, and the Spanish had a hard time keeping it all under control for numerous invading parties. While the pirates were one thing, the Spanish fought established foreign entities, like the British, to keep control. Sometimes, it was the other way around!

The war history is best exemplified with the grand Castillo de San Marcos. It sits longingly over the waterfront. It is the largest and oldest masonry fort in the United States and was a major place of contention. Visit the fort for a reenactment and daily cannon firing.

Pirates Galore!

With the city resting right alongside a river to the ocean, and with so much luxury, it should come as no surprise that the city has an attractive lure for greedy pirates. The St. Augustine Pirate Museum explores the pirate history, with authentic treasure, recreated items of pirate lore, and even pirate film memorabilia. It also houses the only confirmed pirate treasure chest ever found.

Pirates are built into the DNA of the city. Even in its earliest European discovery, people were attracted to the pirate lifestyle and the riches of the area. A group of early settlers actually mutinied, joining a legion of neighboring pirates to overtake Spanish water vessels in and around the Caribbean tied to St. Augustine. This is only a small taste of St. Augustine’s rich water history. Visit the beach outside our St. Augustine vacation rentals and seek your own pirate treasure!

Ghosts and Ghouls

St. Augustine has an arresting history with ghosts, from recent run-ins to classic tales of old. You can hear some of these tales at the Old Jail, a haunted and brooding museum attraction. A stop by the dark room, space where the worst was put for years on end, will leave you breathless. The tour even carries you to the jail grounds, where “visitors” were put to death- daily.

The torture museum is also one of the most appealing attractions for macabre St. Augustine history.  Ghost stories run rampant in these top places to visit.

We also recommend the ghost tours. You can take them by trolley or by walking. The St. Augustine ghost tours take you to some of the most unnerving locations in the city, including the local graveyard (with gravestones dating back over 300 years), the college (with widely-circulated haunts to this day), and the various ghost-sighting spots in the outskirts of St. George Street.

Plan Your Stay!

Come experience the oldest city in America for yourself! Book your trip to St. Augustine today.

Most of these sights and sounds are in St. Augustine’s downtown. You can get to downtown from our beachside St. Augustine condo rentals by taking the Bridge of Lions and entering the city over the Matanzas River. It is about 20 minutes away.

Book your own St. Augustine rental today. Get more than a glimpse of the city’s dense history from afar- see it for yourself.