Welcome to the Jersey Gypsy column, where our resident travel reporter, Valentina, roams the globe in pursuit of stories.
When most people think of Florida, they often picture its warm weather, beaches, theme parks, and wildlife. My parents? They’re quick to remind me about the retirement perks and affordable assisted living — classic mom and dad!
So imagine my surprise when I rediscovered that Florida is home to the oldest city in the U.S.: St. Augustine.
Having always had a keen interest in history, I knew that the city must have plenty of stories to tell. And let me tell you, it certainly does, and I soaked up every bit of it during my visit.
Iconic Landmarks of the Past
Now, I probably didn’t get to dive too deep into the city’s historical places, but I did visit the must-see spots. Honestly, I didn’t plan my itinerary too much. I simply looked up the most popular tourist spots and decided to explore as I reached them.
Castillo de San Marcos
Okay, history buffs, this one’s for you. The Castillo de San Marcos is a must-see for any visitor to St. Augustine. This massive fort was built by the Spanish in the 17th century, and it’s the oldest masonry fort in the continental U.S.
I honestly felt like I time-traveled when I visited. The fort is enormous, and I remember starting at its thick coquina walls. They’re made from crushed shells, and I couldn’t help but imagine how incredible it is that they’ve withstood centuries of storms, battles, and probably a few rogue cannonballs.
I also joined a tour, and one of the coolest parts was exploring the gun deck. There are actual cannons there, still pointed out toward the sea. I could almost picture the soldiers loading and firing them, defending the coastline all those years ago.
Colonial Quarter
Visiting historical landmarks means countless museums. Yes, St. Augustine has plenty of them, but I can say you have to make the Colonial Quarter a priority. This place offers an immersive glimpse of the city’s past with interactive exhibits and costumed staff.
I wandered through the recreated 16th-century Spanish settlement, marveling at the wattle-and-daub houses and the blacksmith shop, where a burly guy with a handlebar mustache was hammering away at a glowing horseshoe.
While the Colonial Quarter gives you a blast from the past, if you’re ever in Houston, you can instead experience a distinctly futuristic, mind-blowing journey by exploring the Houston Space Center. Between musket fire and rocket launches, both offer a kind of history that leaves you speechless.
I got lucky because there was also a musket demonstration during my visit. I watched in awe as a soldier in full regalia loaded and fired a musket. All I can say is, be prepared for a deafening blast that will echo through the courtyard.
Watching it wasn’t enough, though — when I was asked to try it, I didn’t hesitate. The costumed soldier was kind enough to guide me through it, but I have to say, the recoil nearly knocked me off my feet. It was still a blast, as firing a real musket was something I’d never done before.
St. George Street
Outside the museums, the streets of St. Augustine offer an experience of their own. You must take a stroll down St. George Street. This pedestrian-only thoroughfare is lined with charming shops, quirky boutiques, and tempting restaurants, all housed in beautifully preserved colonial buildings.
I spent an afternoon wandering down this cobblestone lane, and it was quite a romantic experience, even on my own. I entered a few antique shops, art galleries, and souvenir stores. I even stumbled upon a “love potion” shop, which seemed a bit eerie, but hey, when in Rome (or St. Augustine, I guess).
The Ximenez-Fatio House Museum
The Ximenez-Fatio House Museum offers a fascinating glimpse into what life was like in St. Augustine during the 18th century. The rooms have been meticulously preserved, allowing you to admire period furniture and intricate textiles while reflecting on the stories that echoed through their walls.
Our guide was a knowledgeable woman in period attire who shared tales of the house’s former residents. I remember she talked about Spanish merchants, socialites, and even a few scandalous figures who once lived in spaces like this.
The Fountain of Youth Archaeological Park
Okay, the Fountain of Youth Archaeological Park is a bit… cheesy. But who can resist the allure of eternal youth? I mean, wouldn’t it be amazing to sip from a magical spring and never age a day?
While I didn’t exactly find the Fountain of Youth (shocking, I know), I had a fun time exploring the park. I learned about Ponce de León’s legendary quest for the fountain, visited a reconstructed Timucuan Indian village, and even tried a sip of water from the “spring” (it tasted like… well, water).
Speaking of must-visit spots, if you’re ever in Texas, don’t miss out on a stroll along the iconic San Antonio River Walk — a whole different kind of adventure.
Outside the Historical Tourist Trails of St. Augustine
Now, it’s not all museums and historical landmarks when visiting St. Augustine. Here are more things you can enjoy exploring.
St. Augustine Beaches
I was already in Florida, so I figured I might as well visit the nearest beach and ended up at Vilano. I’m glad I did because the area seemed quieter, allowing me to enjoy a more relaxed experience. The coquina sand here also gave me an authentic St. Augustine vibe.
Nights of Lights
If you happen to be in St. Augustine during the holiday season, you’re in for a treat. The Nights of Lights is a magical event that transforms the city into a twinkling wonderland.
Wineries
Wineries in Florida might sound surprising, but trust me, they’re worth a visit! The St. Augustine area has a burgeoning wine scene, with several vineyards offering tastings and tours. I visited the San Sebastian Winery, housed in a historic building, and sampled some surprisingly delicious local wines.
Some of the wines even rivaled the hidden gems I discovered while bar hopping in Melbourne, Australia, a few months ago. It was a fun way to experience a different side of St. Augustine.
FAQs About the Oldest City in the US: St. Augustine
What Is the Best Time to Visit St. Augustine?
The best time to visit St. Augustine is during the spring and fall when the weather is mild and the crowds are smaller. However, the city is charming year-round.
How Long Should I Stay in St. Augustine?
When it comes to how long it’s ideal to stay and explore St. Augustine, I’d say a minimum of two days. However, if you want to delve deeper into the city’s history and attractions, you could easily spend a week or more.
What Are Some Must-Try Local Dishes in St. Augustine?
There are definitely a few must-try local dishes in St. Augustine since they offer a variety of dining options. But just like any other place in Florida, seafood is a must! Be sure to try local specialties like conch fritters, shrimp and grits, and key lime pie.
Are There Any Special Events or Festivals in St. Augustine?
St. Augustine hosts several festivals and events throughout the year, including the St. Augustine Film Festival, the Nights of Lights, and the St. Augustine Music Festival. It’s best to time your visit around these events, but you should be prepared for heavier tourist traffic.
Timeless Memories from America’s Oldest City
The oldest city in the U.S. is a must-visit for anyone who wants to be reminded of how rich our country’s history is. Exploring St. Augustine is also a nice break from all the partying in Florida and reminds you that there’s more to this state than meets the eye.
I probably won’t be coming back anytime soon, but if I find myself in Florida again, I’ll consider checking out more museums and historical landmarks. St. Augustine isn’t just a place you visit — it’s one you remember.
Got a suggestion for where Valentina should travel next, or what she should do on his adventures? Reach out to her at [email protected] — she’s always looking for something new to try!
