Last Updated on July 16, 2023
The enchanting city of St. Augustine is a multi-faceted jewel that lights up Florida’s northeastern coast. This town, population approximately 15,000, beckons history enthusiasts, beach lovers, foodies, and travelers alike in search of an unforgettable vacation with its abundance of fascinating things to experience.
Wherever you go, St. Augustine’s history embraces you at every turn.
As the oldest continuously-occupied European settlement in the U.S., St. Augustine presents a rich tapestry of remarkable historical sites, structures, and architectural styles that takes visitors on a journey through time.
My husband and I have delved into St. Augustine’s absorbing history on numerous occasions. Below are the experiences we feel you shouldn’t miss. Despite our many adventures here, there is still much more to discover in this treasure trove of American history.
A Brief History
St. Augustine’s story began in 1565 when Spanish explorer Pedro Menéndez de Avilés established the first permanent European settlement in what is now the United States. The city’s early history was fraught with conflict. Spanish, French, British, and Native American blood darkened the land upon which St. Augustine serenely sits today.
One of the most devastating events to befall the young settlement was the 1586 raid by notorious explorer, privateer, and bane of the Spanish Armada, Sir Francis Drake, which left the city in ruins.
The early 19th century found St. Augustine under Spanish control in the “Second Spanish Period,” and the city flourished both culturally and architecturally. During this time, numerous buildings were constructed that still stand today.
Beginning Your Magical History Tour
With so much to see and do in St. Augustine, I found the easiest and most enjoyable way to familiarize myself with the city was on a Hop-on-Hop-Off, 90-minute narrated Old Town Trolley Tour. This allows access to 22 stops, providing an overview of the city.
Guests have the option to disembark at any one of the stops and catch another trolley later. From this I was able to plan what we could reasonably do during my visit.
Pro Tip: Trolleys have lifts to accommodate wheelchairs and scooters. Tour scripts are also available upon request for passengers with hearing impairments.
Castillo de San Marcos National Monument
Castillo de San Marcos is the oldest masonry fort in the continental U.S. and the focal point of historic St. Augustine. Part of the National Park Service, this immense Spanish fortress was built to defend Spain’s interests in Florida and is St. Augustine’s oldest structure.
The fort’s construction began in 1672 and took 23 years to complete. This wasn’t the first Spanish fort on the site, but it turned out to be the strongest and most lasting. Fort builders used coquina – a locally sourced limestone made of broken shells and corals cemented together – which was fire resistant and impervious to attack.
Thirty years after Castillo de San Marcos’s construction began, the coquina passed its first of several tests under fire. In 1702, British troops burned St. Augustine, but were unable to penetrate the fort’s walls. The British never took St. Augustine in battle, but in 1763, Florida became a British colony via the Treaty of Paris.
However, Florida’s status as a British Colony was short-lived. Twenty years later, the United States gained its independence and obtained Florida after the end of the War of 1812.
Both the British and Americans used the fort as a military prison, first for revolutionaries and then for Native Americans. Castillo de San Marcos was officially recognized as a National Monument in 1924. Thanks to the coquina, Castillo de San Marcos remains magnificently preserved even after more than 300 years.
We took our time exploring the exhibits depicting life within the fort through the centuries in the storerooms surrounding the central courtyard. Then we climbed the stone steps to the gun deck where we lingered over the spectacular views of Matanzas Bay and St. Augustine.
Pro Tip: A self-guided tour of the fort is available through a free app and with an informational brochure in regular print, large print, and Braille. The entire lower level, which houses the museum rooms, theater, bookstore, and restrooms, is wheelchair accessible.
Plaza de la Constitución
Plaza de la Constitución is the heart and soul of the city and has been a central gathering place for locals and visitors since 1573. It derives its name from the obelisk located in the Plaza, which celebrates the Spanish Constitution of 1812.
Bordered by three historic structures – Cathedral Basilica of St. Augustine, Trinity Episcopal Church, and Government House – and facing the Bridge of Lions, Plaza de la Constitución still retains its pivotal role in the city’s history.
The public market, which dates back to the 1500s, is a delight. When I have time to wander, it’s almost as if I can hear 16th century vendors hocking their fresh fish, produce and other wares from makeshift stalls – all in Spanish of course. Today, English-speaking vendors sell a variety of goods from folding tables in this historic marketplace.
Another plaza feature that stood the test of time is a pre-1700s well now designated as an American Water Landmark. And the national recognition continues. In 1970, the town plan and plaza were named a National Historic Landmark.
We enjoy our visits to Plaza de la Constitución not only because they give us time to slow down, but the monuments located throughout offered an opportunity to immerse ourselves in a St. Augustine history and art experience. These include tributes to American Revolution prisoners, as well as monuments honoring soldiers who gave their lives in WWII, the Korean and Vietnam Wars.
The Civil Rights movement is also recognized in this Plaza. Note the marker honoring civil rights activist, U.S. Ambassador to the United Nations, and two-term Atlanta mayor, Andrew Young at the crossing that bears his name.
The Freedom Marchers Monument, with a poignant and powerful inscription, honors the courageous men and women who fought for civil rights in St. Augustine during the 1960s. Known as the Foot Soldiers Monument, this bronze sculpture features four life-size busts representing the demographics of the civil rights activists. They are positioned shoulder to shoulder in front of a relief portraying a protest in the Plaza.
Simply because Plaza de la Constitución is chock full of St. Augustine history doesn’t mean there isn’t an equal amount of fun to be had. The plaza features a central pavilion for public and private events as well as live entertainment.
With its series of summer “Concerts in the Plaza” and spectacular “Nights of Lights” during the holidays, the Plaza is a family-friendly venue with a welcoming vibe.
Pro Tip: Sculptures in and around Plaza de la Constitución are part of the Braille Trail. Braille markers with tactile graphics were developed by the St. Augustine Art Association. A Braille Trail audio guide is also available.
Lincolnville Museum & Cultural Center
One of our most interesting and thought-provoking St. Augustine experiences was the hour we spent at the Lincolnville Museum & Cultural Center. Housed in the 1925 Excelsior High School building that served as the first high school for Black students in St. Johns County, the museum shares the story of Black History in St. Augustine’s Lincolnville neighborhood.
In 1866, an orange grove was divided into small parcels of land that were sold for a pittance to free Black men following the Civil War. We found the detailed exhibit chronicling the lives of Lincolnville neighborhood residents from its inception especially intriguing.
Moving from room to room, we felt as if we were on an emotional rollercoaster. Some exhibits were raw and disturbing, while others were hopeful and uplifting. In the Civil Rights Room, we saw Dr. Martin Luther King’s fingerprint card from his arrest on June 11, 1964. His crime? Trying to desegregate a fine dining establishment.
Along with Dr. King, the police arrested other protesters, including 18 rabbis who joined the protest. Photos don’t lie. Most people don’t realize that St. Augustine was central to the Civil Rights Movement.
Pro Tip: The Lincolnville Museum has guest parking. Handicapped spaces are located at the back and ramps at the front and back of the museum.
Fountain of Youth Archaeological Park
Fountain of Youth Archeological Park is believed to be the site where, in 1565, Spanish explorer Pedro Menéndez de Avilés established the first new world settlement. We spent two hours exploring this magnificent park, but wished we could have stayed all day.
There was a host of things to see and do, but we didn’t even come close to availing ourselves of all the park had to offer. We took in the history reenactments, weapons demonstrations and cannon firing, blacksmith exhibit, and the replica of a Timucua Village.
And of course, we drank from Ponce de Leon’s legendary Fountain of Youth, a natural spring with some of the worst tasting water you can imagine. It had a strong metallic bite, but I knocked back the contents of the small cup and hoped for the best. I can honestly say it didn’t do a thing for me in the youth department.
After meandering along the paved paths in the hot sun, we sat down in the air- conditioned Navigators’ Planetarium – as much to cool off as to see the show. We were spellbound throughout. The presentation demonstrates how 15th and 16th century technology and skillful navigation guided European explorers to our shores.
The finale was a representation of the way the sky appeared on April 2, 1513, the night before Juan Ponce de Leon landed not far from where we were sitting.
Now fully engaged, we wandered to the next exhibit, the two-story Discovery Globe. Standing 30-feet-tall, the globe illustrated the explorers’ routes between the New World and their homelands, the lands of “La Florida,” and the new universities as well as the settlements and cities they founded in America.
We ended our visit relaxing on a bench listening to the squawking of the park’s 30 colorful peacocks and savoring the pleasant water views from the 600-foot Founders Riverwalk.
Pro Tip: Like much of St. Augustine, the park welcomes leashed dogs, so feel free to bring your four-legged friends.
But Wait! There’s More!
I’ve given you a small sample of the historical wonders of St. Augustine, but would be remiss if I didn’t briefly mention others:
- St. Augustine Lighthouse and Maritime Museum: Built in 1865 on the site of the original 16th century structure, this lighthouse soars 156 feet into the sky. Climb the spiral staircase for an unforgettable view of St. Augustine and if you’re lucky, a breathtaking sunset.
- The Lightner Museum: Housed in the former Alcazar Hotel, a grand late 19th century Spanish Renaissance Revival building, the museum showcases Otto Lightner’s extensive collection of art, antiques, and curiosities. You can wander the labyrinth of salt and pepper shakers, cut glass, typewriters, models of all sorts, and come face-to-face with a genuine mummy.
- Flagler College: Take a guided tour of this historic college which highlights the architectural heritage of the former Hotel Ponce de Leon where the institution now stands. Built by railroad magnate Henry M. Flagler in 1888, the site of this once exclusive resort is listed as a National Historic Landmark and considered one of the finest examples of Spanish Renaissance architecture.
A Historic Night’s Sleep
Of course, we had to sleep at some point, and the 1719 family-owned St. Francis Inn, the oldest bed & breakfast in St. Augustine, was the ideal spot. Conveniently located in the heart of the city, the inn was within easy walking distance of attractions, food and shopping.
This charming inn kept us well-fed with a hearty breakfast, a 5:00 PM social hour and after-dinner dessert.
The family also owns Casa de Sueños B&B, a peaceful retreat in St. Augustine’s historic district. This renovated funeral home offers the same amenities as St. Francis Inn with a touch of elegance and style.
Pro tip: St. Francis Inn is pet friendly, but has no wheelchair access. Casa de Sueños has one large wheelchair accessible room with roll in shower, but this property is pet-free.
