The Best Of St. Augustine’s Living History – What Not To Miss

St. Augustine's Living History with a tour of Flagler College

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St. Augustine, Florida is a truly special place that has a special place in history, time and time again. Even better, you can experience it through many of St. Augustine’s living history sights.

No matter what historical period you’re interested in, you’ll find a way to relive history by visiting these St. Augustine sights.

Background of St. Augustine

St. Augustine is not easy to put in a nutshell. Officially founded in 1565 by the Spanish, the city includes their history, plus British rule, a second Spanish period, Civil War, an oil tycoon, and a civil rights movement. Not to mention, the natives occupied the land before Ponce de Leon arrived.

With over 400 years of recorded remarkable history, you can see why the city is alive with the past.

The following covers some of the highlights and what to do in St. Augustine. These are my personal favorites throughout the city, but by no means touches on everything above.

Entrance to Castillo de San Marcos

Castillo de San Marcos

Perhaps the most recognizable part of St. Augustine is the Fort Castillo de San Marcos, along the Matanzas Bay. Part of the National Park System, Castillo de San Marcos is over 340 years old. The fort never fell into enemy hands by force, although it’s stood under six flags.

Walking the grounds around Castillo de San Marcos is free. Occasionally, you’ll see small demonstrations outside of the park.

However, I highly recommend paying the entrance fee and going inside of the fort. I’ve been to the grounds many times, and on a most recent visit was largely impressed with what I found inside.

To start, walking through the gates is impressive as you imagine new soldiers entering their barracks for the first time. Historical artifacts and information are found in the rooms along the base of the inside of the fort. The NPS does a fantastic job of informing and displaying as much information about the oldest masonry fort in the United States.

interior of Castillo de San Marcos St. Augustine's living history

And if you still don’t get enough out of a visit to Castillo de San Marcos, stay for a canon and weapons demonstration at the top of the fort. Be prepared to cover your ears!

Adults are $15 and children age 15 and under are free. Castillo de San Marcos also honors the interagency passes through the National Park System.

boy drinking from the fountain of youth

Fountain of Youth Archaeological Park

The Fountain of Youth is more than just a gimmick to drink from the mineral waters acclaimed to bring everlasting youth. While the archaeological park offers drinks from the spring, it also demonstrates various living history exhibits such as the Timucuan village, the Nombre de Dios  Mission, a blacksmith, a boathouse and cannon firing.

Depending on the time of year, excavations happen around the park. well. This site was home to many native Americans, the Timucuans.

Don’t hesitate to ask questions of the reenactors and demonstrators located around the park. These folks have a wealth of information to share about their trade and the people who lived on those grounds hundreds of years ago.

Advanced Tickets at the Fountain of Youth are $17. Consider one of the special packages with combo tickets here too.

Flagler’s Influence

To those outside the area, the name Henry Flagler might not be as recognized as John D. Rockefeller. However, as the co-founder of Standard Oil, he made a large impact on St. Augustine and the surrounding areas.

Flagler visited St. Augustine in the 1880s and saw a need to develop a charming city. He built the Ponce de Leon Hotel, which is now part of Flagler College. Additionally, he developed the Florida East Coast Railway to make transportation to the city easier.

He also built the Alcazar Hotel, now the Lightner Museum and he bought the Casa Monica Hotel.

Historic Tours of Flagler College and the Lightner Museum offer an insight into the grand design and architecture that Flagler brought into the city.

Civil Rights Movements

It’s hard to think of the ancient city as part of recent history, but St. Augustine played its part in the Civil Rights movement as well. Dr. Martin Luther King, Jr. along with Dr. Hayling organized protests and a sit-in at the local Woolworth’s lunch counter on King Street. The location is now home to the Wells Fargo bank, but you can still see the original Woolworth’s door handles. The bank also has a lunch counter in the lobby open to visitors during business hours. A monument is also located nearby in Plaza de la Constitucion honoring the foot soldiers of the Civil Rights Movement.

soldiers demonstrating musket shootings in a historical reenactment as part of St. Augustine's living history


This is my favorite part of St. Augustine’s living history. No matter the weekend, you can almost always find a reenactment in the city.

Recently, my son and I visited in order to watch Drake’s Raid. Drake’s raid is a battle reenactment of the anniversary when Drake ransacked and burned the city in 1586. Actors portrayed historical encampments, marching and shooting training, and demonstrations resulting in the battle on the streets of St. Augustine. What’s unique about this particular reenactment is the location. It’s not limited to one location or encampment in the city, and you’ll likely see “soldiers” training near the cemetery or walking St. George Street.

I highly recommend these books when seeking out reenactments in St. Augustine, and other areas of Florida.

  Walking St. AugustineTime Traveler's guide to Florida .  Historical Travelers Guide to Florida

Ghost Tours of St. Augustine

Yes, you can even get a historical perspective on St. Augustine by taking one of their many ghost tours. Whether or not you believe in ghosts, the stories of the persons behind the ghost stories nearly always have a historical significance.

During one such tour, I learned about the number of bones buried beneath the streets. Because cities are rebuilt after storms, buildings are repurposed, and the fact this city is hundreds of years old, burial grounds likely exist everywhere. During recent back-to-back hurricanes, St. Augustine experienced an extensive amount of damage and flooding. However, once such clean-up beneath A1A Aleworks discovered bones that date back to the 1570s. See the discovery here.

Ghost tours, in their own special way, give an inside “living” history that you won’t experience in a museum.

Available Tours in St. Augustine

History while Getting Around St. Augustine

In the historical district, parking is scarce. I’d highly recommend taking one of the two trolley tours offered in the city. Not only do you get a comfortable ride to the city’s attractions, but you’ll also get a guided history tour while you’re at it.

The Red Train Tours are not scripted. Ripley’s Believe it or Not runs the Red Trains and you can park at the museum. They are hop-on-hop-off. Take a map and look for the signs throughout the city.

The hop on hop off Old Town Trolley Tour includes admission to the Florida Heritage Museum as well.

On one of the trolley rides, we learned more about the history of the city, including insights on Flagler and even a jaunt through the Lincolnville Historic District, home to freedmen after the Civil War and an important part of the Civil Rights Movement.

These are just a small part of St. Augustine’s living history. Visiting St. Augustine, Florida provides a glimpse of nearly every facet of American history all in one place.

Eating in St. Augustine

When you’re done touring all around, make sure you check out St. Augustine’s food options. One of my favorite’s is Athena’s on this list.

You may also like other living history sights around the US, found here

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the best of st. augustine's living history

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