America's Oldest City

There are many reasons why St. Augustine feels like a European city, and that European aura and influence dates back 200 years. The story begins in 1513 when Juan Ponce de Léon came to these shores and claimed St. Augustine as the property of Spain.

In the age of the conquistadores when the Spanish began discovering (and pillaging) silver and gold in Mexico and Peru, there were many ships filled with those treasures that stopped off the coast of Florida before making the daunting return voyage across the Atlantic. As a result, the Spanish needed to protect these fleets that sailed along the shores; to assure they had at least a temporary safe haven.

Pedro Menéndez, known as the founding father of St. Augustine, was therefore sent by King Phillip of Spain to drive out the French garrisons that had recently established a foothold in this part of “The New World”. Along with more than 700 colonists and troops he landed on these southern shores with the purpose of building a fort and a settlement to protect Spain’s investments. Like so many other early American colonists, these people faced starvation, harsh conditions, and pirate attacks; but they managed to create a successful settlement.

It was the Spanish admiral Pedro Menéndez de Avilés who on August 28, 1565 (the feast day of St. Augustine de Hippo) officially founded the city, naming it in honor of the saint. This achievement has earned St. Augustine the title of “America’s Oldest City”; this nation’s oldest and continually occupied European settlement. There were other settlements in the area before this but they all failed.

This city has no shortage of battle scars. In 1586, Englishmen Francis Drake burned the town to the ground, but it was soon rebuilt. In 1668 St. Augustine was nearly destroyed again by a pirate named John Davis. Yet again there were no quitters here, and by order of Queen Regent Mariana of Spain, construction on a new stone fort called Castillo de San Marcos began in 1672; the construction continued for over 23 years. The fort was built of coquina, a locally quarried shell-rock which was ideal because it did not crumble under cannon fire. The fort still stands today and is the oldest man-made National Monument in the United States.

Like a tattered and battered veteran of war, St. Augustine was sacked again in 1702 when English troops laid siege to the new fort. For 50 days, the fort was fired upon, and 1500 citizens fled their settlement to the security offered by the new coquina fort. Eventually, the British gave up, but before they left they burned the rest of the town to the ground. This is why there are no buildings in the city today that have been around longer than 1702.

Once again the Spanish refused to give up, and began reconstructing their settlement. Again in 1740, the English attacked and a 27-day siege ensued. Another stalemate followed, and eventually the English once more gave up trying to break through the formidable defenses of the newly fortified walls and fort. With their powerful cannons, the English had launched a heavy attack on the fort but the coquina simply absorbed the cannon balls without breaking apart.

However Spain’s fight for dominance in this part of the Americas would again be forestalled. In Europe, the Seven Years War ended in the defeat of Spain by the British, and in 1763 the Treaty of Paris (often referred to as the Peace of Paris or simply the Treaty of 1763) determined that it would be England’s flag that flew over St. Augustine.

England divided the territory into two segments and St. Augustine became the new capital of East Florida. The latter geographically strategic area remained loyal to the British Crown throughout the American Revolution.

But England’s occupation only lasted 21 years; and St. Augustine was then returned to Spain as part of the negotiations that concluded the American Revolution. By the second Treaty of Paris in 1783, the United States was recognized as an independent nation, with British Canada to the north and Spanish Florida to the south. The western boundary was the Mississippi River.

For the next 37 years, Spain ruled Florida. However there was a great reluctance on the part of Spanish settlers to leave Spain to battle the unknown, especially since a chaotic state of affairs existed in the area. Violent clashes were occurring between American-born settlers, Spanish citizens, British agents, and Native American people in West Florida. This was followed by the arrival of Andrew Jackson who, ignoring the international border, burned native villages and executed two British subjects. He then proceeded to capture St. Marks and Pensacola. The whole situation was finally sorted out in 1821 when Florida was transferred from Spain to the United States by the Adams-Onis Treaty. Jackson became the Governor of this new U.S. Territory.

Peace in the area, however, was not to last all that long. During the 1830s, the federal government and the Seminole Indians began to clash in what has come to be known as The Seminole War. The Seminoles were eventually defeated and Florida became the 27th state of the Union in 1845.

Sadly, from 1875-1887, Native Americans from the Southwest and Great Plains regions were captured and imprisoned in the fort in St. Augustine. The government sought to educate them, granting certain freedoms which some historians and other observers have deemed actions that led to progressive Native American governmental policies. Despite this dark period in St. Augustine’s history, the city continued to flourish.

Over 200 years St. Augustine has endured fire, turmoil, and strife. Five different flags have flown over the city, and today you can still see each flag flying in St. Augustine, a symbol of each part of the tale.

Just as Rome wasn’t built in a day, St. Augustine took hundreds of years to become what it is today. It is a city of many contrasts and cultural richness. Everyone from Spanish colonists, British rulers, Native Americans, freed slaves, and people just passing through have had a dramatic impact on this place. In fact, as I reflect on what I have learned about St. Augustine, I find it incredible that the beautiful 200-year-old buildings for which the city is so well known, are still standing. This is a city that seems to be able to withstand anything. Its stormy and turbulent past is in part what gives it its grand presence today. And this presence is in every historic home, museum, shop, restaurant, bed and breakfast, and monument. Each part of St. Augustine expresses its own piece of the history of this city.

Since so many of St. Augustine’s early buildings still stand, you can experience a much richer, older history (through architecture, art, stories, and people) than you would in other cities of the United States. The Spanish colonial influence is still much in evidence as you walk through the streets of this town.

For a short time during my visit, I almost forgot that I was in the the United States. It was as if I was in a European town with cobbled streets, stunning architecture, exotic culinary treats, tempting boutiques, a serene natural setting — and most importantly, illuminating stories from the past.

Historical sites in St. Augustine that stimulated my imagination

Understanding the who, what, where, and when of history is important to gaining a perspective on an archival destination such as St. Augustine. However in my experience, the imagination also plays an important role. In such experiential and life-long learning destinations, I find that I inevitably experience a need to see through my mind's eye the events that occurred here; and to sense the people who inhabited the place in centuries past. In St. Augustine, this kind of full integration of the senses and the mind is very much a part of the travel experience.

Castillo de San Marcos National Monument

The Colonial Spanish Quarter

The Oldest Wooden Schoolhouse in the United States

The Oldest House in the United States

St. George Street (shops, restaurants, and all the history of the Spanish quarter

Ponce de Leon’s Fountain of Youth

The evocative architecture of St. Augustine

Henry Flagler had a profound impact on the architecture of St. Augustine. The co-founder of Standard Oil (along with John D. Rockefeller), he was of course incredibly wealthy and first visited the city during the winter of 1888-84.

He was immediately charmed by the area and thought the city had enormous potential. However, he found the hotels and public transportation inadequate for what he recognized as a potential travel destination. He was so passionate about his ideas that he ultimately gave up his day-to-day responsibilities at Standard Oil to pursue his projects in St. Augustine. He built the 540-room Ponce de Léon hotel and then purchased the Jacksonville, St. Augustine & Halifax Railroad, the first section of what would eventually become the Florida East Coast Railway. Although he has been called the “Father of Miami” and was involved in many other aspects of Florida’s history, I believe his influence can best be seen in St. Augustine.

Some “Flagler”architectural points of interest:

Flagler College (Formerly the Hotel Ponce de Léon built by Henry Flagler)

Casa Monica Hotel (Formerly the Cordova Hotel built by Flagler)

Lightner Museum (Formerly the Alcazar Hotel built by Flagler)

Memorial Presbyterian Church (Built in 1889 as a memorial to Flagler’s daughter)

St. Augustine as an art lover's mecca

It’s no surprise that a place that is so rich in culture and beauty has inspired artists over the years. In fact, from the 1930s through the 1950s, St. Augustine had a thriving arts community that attracted hundreds of artists. The city eventually became the largest art colony in the southern U.S. through the efforts of a small group of artists who founded the St. Augustine Arts Club in 1931. In 1934, it changed its name to the Arts Club of St. Augustine and then became the Art Association of St. Augustine in 1948. Local businessmen and retailers who understood that cultivating the arts was a way to promote economic development supported the association. Today, the arts community is still flourishing with over 25 galleries and studios in the area.

Some arts “destinations” in St. Augustine

The St. Augustine Art Association (Changing competitive shows, plus permanent collection gallery)

Butterfield Garage Art Gallery (Contemporary work by award-winning member artists)

Absolute Americana Art Gallery (Original artworks from influential 21st century artists; includes a permanent exhibit of Pierre Henri Matisse)

Carrera Gallery (The art gallery of Flagler College)

The culinary culture of St. Augustine

One of the best ways to discover a destination's a story is by experiencing its culinary possibilities. All of the ethnic groups that have passed through this city have left their mark, and dining in St. Augustine is a gastronomic experience par excellence. Spanish, Italian, French, Greek, German, Asian, Swiss, and Southern Florida Cracker are all represented here. Fine dining, casual eating, and gourmet bistros are everywhere, and many of feature world-renowned chefs.

A few that I highly recommend

Palm Café & Bakery (Chef Aaron Miles, features gourmet dining and a relaxed ambiance.)

Kingfish Grill (Fine cuisine and a beautiful view of the Intracoastal Waterway)

Claude’s Chocolate (Hand-made chocolate by a renowned French chef)

Athena Restaurant (St. Augustine’s premier Greek restaurant)

“Organic” St. Augustine

Enjoying the great outdoors is a part of the authentic St. Augustine experience: hiking, biking, kayaking, sailing, shell collecting, parasailing, fishing, and surfing are just some of the activities available for outdoor enthusiasts. A quiet walk on the city's pristine beach will clear your mind. During a sea kayaking excursion, my tour guide regaled me with tales from St. Augustine’s past. Floating on the surface of the ocean in a kayak is such a calming and serene experience; and a welcome break from the intense and thoughtful sightseeing tours.

For outdoor enthusiasts

Kayak tours (One of my favorite activities)

Nature Boat tours (A great way to see dolphins)

Schooner Freedom (A romantic sail on a replica of a 19th -century schooner)

Ghost Tours (A great way to enjoy the night air and some thrills and chills)

The Red Train (Catch the Red Train and learn the layout of the land; and a lot about history)

Classic accommodation in St. Augustine

There is no shortage of unique places to stay in St. Augustine. The most fascinating places (in addition to Henry Flagler’s hotel legacies) are the quaint and often mysterious bed & breakfasts that are everywhere in the city. For a more personal experience, I recommend staying at one of the latter. Almost all of them are stories in themselves, and their owners have a lot of genuine pride as well as knowledge about their hometown. Along with beautiful furnishings, quiet ambiance, and luxury treatment, all of these bed and breakfasts have something different to offer. The fact that some of them are haunted only adds to the lure of each place.

Places to stay

Casa de la Paz

St. Francis Inn

Bayfront Marin House

Bayfront Wescott House

Inn on Charlotte Street

Casa de Solana

Casablanca Inn

Enduring St. Augustine

It is no wonder that so many people choose to return to St. Augustine time and again. There are so many layers to uncover in this city. St. Augustine is what I love most about the places I’ve been to in Europe; the elegant beauty of blending the old with the new; the integration of history and culture; and the very real effect this meaningful atmosphere has on the people of St. Augustine. This is a thoughtful city. How fortunate for me that St. Augustine happens to be in my part of the world.

For More Information

The Official Website for the City of St. Augustine

St. Augustine's Old City

St. Augustine, Ponte Vedra & The Beaches Visitors & Convention Bureau


St. Augustine: A European Travel Experience in Florida
by Stephanie Moreland

There are a lot of things I didn’t know about St. Augustine. However, I could find it on a map. I heard that it was near some terrific beaches. And I had some vague awareness that there was a whole lot of American history contained in this relatively small area. So when I planned a trip to St. Augustine, I knew there would be some surprises in store for me. But I had no idea that I would leave this city feeling as if I had been immersed in a grand and momentous European destination.


Photographs by Stephanie Moreland