Oldest City Around, St. Augustine

Crucial Coffee Cafe

Stumbling upon St. Augustine was really a treat. After a tiresome drive from the northeast, we knew that we wanted to rest in the north of the peninsula before making our way to Miami. Having heard of St. Augustine before but with essentially no specific information, we booked a room at the beach at the last minute. We arrived late at night so our first glimpse of this city was the next morning. At first, St. Augustine seemed like a quaint and quiet beach town. Luckily, I had an insatiable craving for waffles that morning and we realized that the closest waffle establishment was a 20 minute drive away. Taking that drive was one of the best decisions on our road trip from New Jersey to south Florida.

After about a 20 minute drive, we found ourselves amidst a quaint and historic town unlike any I have seen in the United States. The narrow streets were lined with historic landmarks and artisan shops. This city felt reminiscent of New Orleans with a Spanish flair. After learning a bit about the history of this city (the oldest in the US!), the architecture all made sense. St. Augustine was first settled by the Spanish nearly 200 years before the Declaration of Independence was signed.

Castillo de San Marcos


  • Castillo de San Marcos: This seaside fort is worth a visit. Although the fort itself is pretty simple, there are many interesting and informative placards. Did you know the fort was occupied by the Spanish about 150 years before the United States was established? It is also a national park, so you can get a stamp for your national park passport too!
  • Exploring the quaint historic section: Simply walk around and get lost through the narrow roads and passageways while exploring interesting shops and historic sites such as the oldest wooden schoolhouse in the US. You can easily spend a day aimlessly exploring.
  • Cousteau’s Waffles and Milkshake Bar: Who knew that a delectable treat would lead us to discovering the historic section of St. Augustine. The small size of this shop does not take away from the delicious and unique variety of waffles. Ever try a smores waffle? If you wear a red beanie you get 10% off your purchase!
  • Crucial Coffee Cafe: This tiny cafe is definitely worth a visit. The tiny inside is lined with humorous art and trinkets while the lush outside seating is lovely. Although St. Augustine can be quite busy, you can hide away among the greenery and enjoy a nice cup of tea.

Crucial Coffee Cafe

Potato Thoughts

I am happy to say that waffles made it all happen. We nearly utilized St. Augustine as simply a layover on a long drive until we set out on a pursuit for waffles. The unique selection of waffles at Cousteau’s Waffle Bar was a lovey find. As per usual, I also really enjoyed simply walking around and getting lost among the narrow roads of St. Augustine’s historic district. By exploring these roads, we found the oldest wooden school house in the U.S. You can a visit this small attraction for about $5, which includes a diploma commemorating your visit.

The fort Castillo de San Marcos was a highlight for its great view of the town and for the interesting placards within. I really enjoyed reading about what life was like at this fort 150 years before the U.S. was established. In particular, it was fascinating to read about the ways in which indigenous individuals participated in the fort. After exploring for hours we stumbled upon Crucial Coffee Cafe, which is another highlight. This coffee shop has a wide array of beverages and even ice cream that you can enjoy inside the funky shop or amidst the lush greenery outside. St. Augustine was such a lovely surprise that we have been back for another visit!

Couseau’s Waffle & Milkshake Bar

Dino Thoughts

The Castillo de San Marcos was the highlight of the trip for me.  I enjoyed roaming around the oldest fort in the oldest city in America. It’s a national park, meaning the fort is staffed with friendly park rangers in spiffy hats.  The $10 entry fee is good for 7 days.  You can wander the fort on your own or take a tour with a ranger.  We opted to explore on our own, ducking into the chambers of the fort and reading the cryptic writing on the walls. There’s literally writing on the walls scribed 300 some years ago. After exploring the lower lever of the fort, we made our way to the top of the fort walls. Once on top, you are greeted by a 360° view. The Matanzas River, Tolomato River and Altaic Ocean meet in front of you and St. Augustine sits behind you. The view is wonderful…so wonderful we forgot to take any pictures of it. I did manage to snag a picture of the ocean though a gun port in one of the turrets.

Castillo de San Marcos

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