Although I’ve known of St. Augustine’s claim as “America’s Oldest City,” I grappled with the immensity of this fact during a lovely, but chilly, day trip with my friend, Jimmy. He had recently bought a car there and needed to pick it up, so he asked me to tag-along. Although I didn’t need any convincing to join in on a road trip or to explore a new city, he promised me two things: ☝🏽-we would have a good time and ✌🏽-I could drive the new car back. Then, he refused to tell me anything else — except that I would enjoy the day 👌🏽
Fun fact: St. Agustin was founded in 1565 & is recognized as the oldest continuously inhabited European settlement of the continental U.S.
From time to time, Jimmy works in St. Augustine, so he’s become pretty familiar with the area. After picking up his new baby Benz, we parked both vehicles off Marine Street, right behind the Post Cemetery and Saint Francis Barracks. This historic building, originally a Franciscan convent monastery, was converted for military use in 1763 and now serves as the headquarters for the Florida National Guard. On most days, it’s restricted to “authorized personnel” (i.e., those with the appropriate credentials and clearance) but, that Saturday, was my lucky day — we were granted access 😬.
Jimmy was a gracious tour guide as we walked the premises, allowing me to examine every framed National Guard accolade and each of the gloriously patriotic, yet strikingly strange, painted war depictions as we walked from one wing to another. In the middle of the establishment, is an open-air courtyard, where we observed event planners busily setting up for a wedding that was to be held later that evening. We tiptoed past their delicately hung string-lights and entered another building that secretly boasts a history museum.
This tiny, three room exhibit proudly reveres Florida’s National Guard’s soldiers and leaders since the time of the city’s official founding in the early 1900s. At it’s entrance, stand two fully-preserved wooden-plank doors (you know, the type that are usually typically cast as the protectors of gun powder and cannon balls in pirate movies). They stand in stark contrast to the original stone walls seemingly stand guard over the artifacts, relics, and identities of those preserved inside.
Pro Tip: when planning your trip to St. Aug, contact the St. Francis Barracks’ historian to arrange a tour of this hidden gem. It is occasionally open for the public.
Across the narrow street outside of the military compound lives the Gonzalez-Alvarez House – aka “The Oldest House”, a national landmark that offers a glimpse into what life was like here 300 years ago. We stepped inside the entrance (which is also the museum store) and were greeted by a curiously sweet curator behind the counter. She was so knowledgeable in all things uniquely St. Augustine and graciously offered her recommendations for the city’s “must sees”. Although we weren’t able to make it this time, she encouraged us to attend a meet and greet with a Minorcan citizen (who is typically scheduled to be on location from 12-2 PM) to learn first-hand about the town’s native people. I’m still sad that we missed this cultural opportunity, but I’ve already prioritized for my visit!
Interestingly, I was most intrigued to learn about coquina (a sedimentary rock almost entirely comprised of fragmented shells) that was used a construction compound throughout much of the St. Augustine settlement. It’s natural strength and durability enables it to withstand nearly all natural elements (e.g., the sun, ocean water, and winds) and manmade hazards (i.e., bullets or intentional fire) – something of great value to the early inhabitants, particularly those whose home in which we were standing. I’m not sure if it was because of my obvious fascination or our host’s cheery disposition, but she allowed us to more closely examine the material by stepping outside into the rock garden, where a cannonball was literally lodged into the unyielding coquina wall. Seeing it’s defensive powers firsthand, I no longer wondered how the city’s walls could have remained intact and standing tall despite it’s tumultuous history.
After saying farewell, and sincerely hoping to see each other again, Jimmy and I set off to explore the historical district on foot. We passed through the Plaza De la Constitucion, a pavilion park characterized by an old water well, a small civil rights monument, and a public market space (where just one vendor was braving the cold to sell air plants). We followed the sidewalks and navigated between the local traffic to arrive at Ponce De Leon’s feet. He stands tall, in the midst of a modern city, historical ruins, and a timeless oceanside skyline, overseeing the rewards of his most famous expedition. As we passed informational markers and stops for the self-guided walking tours, the school psychologist in me was curiously impressed to see that they all included Braille and audio options! This was certainly a testament to the town’s consideration and inclusion of those who visit, particularly the students and guests of the Florida School for the Deaf and Blind #Equality & #Inclusion ❤️❤️
We continued our trek down A1A and tried to envision the exact disembarkation spot of La Florida’s founder, but were quickly distracted by a laminated photograph posted on wall depicting the flood line level, which resulted from Hurricane Matthew’s arrival in October of 2016. My head, like much of storefronts around me, would have been completely submerged underwater. That realization prompted me to said a little prayer for continued protection, from man and Mother Nature, so that visitors and locals alike can continue to enjoy the city for centuries to come #LongLiveStAugustine.
The crisp morning air, however, brought me back to our current mission and prompted Jimmy and I to walk at a brisk pace until we reached Castillo de San Marcos. I’ve walked the perimeter of this national monument before, but had never gone inside. Thanks to his National Park pass, we crossed the drawbridge above the dry moat and entered through the portcullis. We read each historical fact posted on the informational signs, searched each of the gundeck cannons to identify their dates of production (some reaching as far back as the 1760s!), and did our best to decipher the images and writings etched into the compound’s stone walls by soldiers on duty to protect this fort. We were also fortunate to encounter local volunteers who dressed and replicated the lives of those whom these walls stood to protect over the past few centuries. Of course, I couldn’t leave without finding the official cancellation stamp to commemorate this visit in my National Parks Service passport 🤓
Struggling to bare with the cold and our growing hunger, we decided to mosey down St. George street – the city’s historic downtown district. Although highly commercialized, the area is quaint and, occasionally, local. The cobblestone streets are lined with shops, historical sites, tourist traps, bakeries, ice cream shops, and restaurants. We chose to stop into the Florida Cracker Cafe to get a taste of the local fare. Everything we had was delightfully tasty, but I most appreciated the warmth that was restored to my body after a cup of their Minorcan Clam Chowder.
We decided to walk off our lunches by peeking into the immaculate lobby of the Flagler State College. Despite the size of it’s student population, the institution and it’s architecture couldn’t be described in any other way but grand. It’s truly a breath-taking marvel, so much so that I regretted not knowing about it during my own college search and application period. Across the street, stands the majestic Casa Monica Resort & Spa. Jimmy and I marveled at the exterior design of this beautiful hotel before deciding it was unfortunately time to make our drive back home across I-4. Since we were still a few blocks from the parking lot, however, we decided to take the scenic route and visit a few more localities on the way – taking in every bit of charm this charming historic town has to offer. If the allure of finding the famed fountain of youth isn’t enough to compel you to visit, at least come to appreciate the pleasing character embodied by all the hidden gems of America’s Oldest City.