Road Trippin: A St. Augustine Photo Essay

As a teacher, I plan my entire school year around holidays. Myanmar for October break, Belize for winter vacation, Bali for Chinese New Year. I can’t help it; I’m an eternal wanderlust.

However, something was different at the end of this school year. The thought of traveling exhausted me, and I wanted nothing more than to spend time with family and friends in Florida. Plus, after a year of learning the IB curriculum and navigating my way through Chinese culture, the only plans I wanted to make involved my parents’ pool and a lounge chair.

But quickly after I arrived, my friend Nick told me about his desire to see more of Florida, and suggested we take a road trip to St. Augustine. Since I hadn’t been since I was little, spending a couple of days exploring the “Nation’s Oldest City” seemed worth leaving the pool for.


St. Augustine was founded in September 1565 by Don Pedro Menendez de Aviles of Spain. It’s actually the United States’ longest inhabited European-founded city. So, there’s your fun fact of the day.  Above, you will see the historic narrow lanes, traditional shops, and the dorkiest picture ever: Nick and me (two teachers) with our “diplomas” from touring the nation’s oldest wooden schoolhouse. Word to the wise: unless you love schools, or just have an extra $5 burning a hole in your pocket, skip it. 

Castillo de San Marcos, on the other hand, was pretty impressive. It’s the oldest stone fort in the continental U.S., originally built by the Spanish between 1672 – 1695. Also, it’s on the water, so it’s pretty.

I know this is super touristy, but I loved the Pirate & Treasure Museum. Admittedly, I have a strange obsession with pirates (I blame it on being from Tampa), but I’m pretty sure anyone would enjoy seeing 400-year-old treasure chests filled with gold. It’s supposedly the largest collection of pirate memorabilia in the world. 

Another highlight was taking the St. Augustine Distillery tour. First, it was free. Second, they gave away free booze. And third, the distillery is connected to prohibition-style Ice Plant Bar. Let me tell you, those drinks are legit. I recommend the Florida Mule

The end of day one consisted of Dole Whips, BBQ and whiskey at an amazing place called Mojoand a ghost tour (I couldn’t help myself). The ghost tour was actually worth it, as we learned a lot about the town’s history and had a chance to see the town at night. I don’t think I need to tell you that the beef brisket and bourbon were worth it. Nor the creamy pineapple treat.

The next day we headed to the lighthouse and to Anastasia State Park. We didn’t pay the $10 to go inside, but we did pay the $8 to get into the park. And it was worth it. Just look at the view.


The rest of the day was spent meandering around the old streets, eating delicious gourmet popsiclespopping into used bookstores, and eating at The Floridian restaurant. It was a pretty good two days.

Tell me: Have you been to St. Augustine? What’s your favorite thing to do?

18 thoughts on “Road Trippin: A St. Augustine Photo Essay”

      1. haha… I love Nick’s comment here.

        Welp, looks like you guys had the perfect little visit because, let’s be honest, nothing beats pirates and popsicles. These are gorgeous pictures, Jennifer!

        1. Yeah, he was pretty clever, Margo! And thanks for the compliment. I totally agree with you. xo

  1. Traveling within the states can be very rewarding. Last summer, while traveling up the coast, we stopped for lunch in St. Augustine. The pub/sidewalk cafe was more than I had expected. I ate shrimp and grits, drank a few local IPAs and listened to a very talented young man play and sing songs from the 70s. Oh yeah, we loved our afternoon in the oldest city!
    When I travel (anywhere) it is all about the food, the people and their culture. As I experience various areas of the USA I find it difficult to believe we are all lead by the same government.
    I enjoy your blog. Come out and visit me…you can write about the cowboys!!!

    1. Thanks for sharing that wonderful memory, Patty! I agree, and also travel mostly for food, but fall in love, over and over, with the people and their cultures. Travel is a gift, and I’m glad to see that you see it that way too. My parents speak very highly of you and say I must meet you one of these days. I hope to do so. Thanks for reading.

    1. Haha I love fun facts of the day, Carmen! Thanks so much for reading. I love Florida, but I’m a bit biased 🙂

    1. Danielle, it’s actually a beautiful place, in northwest Florida. It’s about an hour north of Daytona, on the coast. Thanks for reading! 🙂

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