St. Augustine: America’s Oldest City

St. Augustine - America's Oldest City

When travelling, there are always locations that I look forward to more than others. These are the places that I meticulously plan and prepare for because I want to be able to get as much out of them as possible. Places I’ve dreamt of visiting for a long time such as Austin or New Orleans. The kind of places that top my bucket list for years before I finally make a point to get there.

Then there are the places and their moments that are discovered in a completely organic way. The bits and pieces that leave a smile on your face and create stories to tell your friends and family when you arrive home. The joy of driving across the Golden Gate Bridge for the first time. Having your first kolache in Houston and craving a dozen more. Meeting the caretaker of Lafayette Cemetery and having him take the time out of his day to give you a personal tour.

St. Augustine, Florida was such a surprise to us. We first heard about it when discussing the last leg of our trip with my Aunt; we were leaving Orlando, stopping in the Everglades and then heading up to Jacksonville for a final night in Florida. She mentioned that we should stop in this little town just south of Jacksonville and at least walk around the downtown area, if nothing else. It was really pretty and full of history, two of the most important things we look for when we are planning a trip. And Ryan and I had just agreed to always take the advice of locals when it’s given, and my Aunt definitely qualifies as a local.

After a disastrous night in the Everglades, we needed pretty. Rejuvenation was needed because we were certainly feeling down. We had a million bug bites and about two hours of sleep between us, and it would have been sad to end our road trip on a low note. Our stop in Jacksonville was only to sleep before driving 13 hours to Pennsylvania. We needed a high note, and St. Augustine provided just that.

St. Augustine sits about thirty minutes south of Jacksonville, right on the Atlantic Ocean. Having been founded by the Spanish in 1565, it is the US’s oldest permanently occupied European settlement. On August 28, 1565, land was sighted by Spanish explorers. Over a week later, on September 8, Don Pedro Menendez de Aviles came ashore; the little inlet where he landed was named St. Augustine, after the Roman Catholic saint whose feast day occurred on the day land was seen.


Old City Gate, looking down St. George Street
Old City Gate

Upon our arrival, we parked near the visitor’s center and walked through the Old City Gate towards St. George Street. In 1704 construction of the Cubo line, a powerful earthen wall supported by palmetto logs, was started. This was built to help protect the city from enemies. The Old City Gate that currently stands dates from 1808, the last time the Cubo line was reconstructed. The gate marks the top of St. George Street, a pedestrian thoroughfare and the heart of St. Augustine.

St. George Street, a perfectly pretty place to walk!

What I loved the most about this city was the feel of being surrounded by history. We walked down St. George Street, stopping to read the markers on the buildings and enjoy being able to meander wherever we wanted. That’s the nice thing about having designated pedestrian areas; I feel like I’m actually able to really take my time and immerse myself in history, without worrying about my safety when I get complete distracted! All of the older buildings had markers talking about when the building was built and what it’s original purpose was.

We passed the Cathedral Basilica of St. Augustine and paused in the Plaza de la Constitucion. We didn’t have any specific route in mind, and soon found ourselves continuing down Aviles Street, the oldest street in the city. It was much more quiet than St. George Street, but no less beautiful.


This street is not pedestrian only, watch out!

The renaissance of St. Augustine started in the 1800’s with the arrival of Henry Flagler, who constructed a few opulent hotels in the city. These hotels are not only still standing, but have been re-purposed; Flagler Hotel is now Flagler College and Alcazar Hotel is not the Lightner Museum and City of St. Augustine offices.  We passed by both of these old hotels on our walk around the city.

The old Alcazar Hotel
The old Alcazar hotel, now a museum and offices
The Flagler Hotel, now Flagler College

We ended our time in St. Augustine by walking around the Castillo de San Marcos. The Castillo is a large stone fortress that was built to protect St. Augustine. The fort took 23 years to build and is the oldest building in St. Augustine at 315 years young. Made of coquina (soft limestone made of broken shells), it is fireproof and has been proven to be impenetrable to any enemy attacks.

Castillo de San Marcos


Original cannons outside the Castillo walls


The drawbridge view from the Castillo


We made it to Jacksonville just in time to make dinner and get some sleep. Tropical Storm Colin was due to hit Florida the next morning, so we wanted to get as early a start as possible. It was surreal to actually be in the final night of our trip. We didn’t do much talking that night, I think we were both lost in our own thoughts and reflecting on the last three weeks.

In retrospect…

Looking back on all of the places we visited and all of the things that we did, I think it’s safe to say that I’ve never had such a fun trip. In total, we drove over 5,000 miles and spent 110 hours behind the wheel. We saw nine different cities, five national parks and one World of Harry Potter. I ate a ton of good food, witnessed a rap battle and rode in a golf cart. Bears, armadillos and crocodiles were all seen.  There has been plenty of laughter, a few tears, too many bug bites and a bit of sunburn.

I know that the rest of the year will be full of new and exciting adventures, but having the chance to travel across the United States and stop and see so much of it has really been life changing (as cliche as that sounds). We’ve had three weeks at home to decompress and wind up for the next part of our journey. I’d love to hear how travel has changed your world views!

The next few days will be busy with getting everything ready for our departure to Scotland on Thursday! I can’t believe how time flies!

Until next time!

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    1. I would say you did it great justice, other than you don’t think they are as rave-worthy as I did 😉 You described the pastry perfectly though, so I’m going to have to use your description when people ask me about them next time!

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