Saint Augustine, Florida: a Magical Day in the Country’s Oldest City

Wander HereUSA Roadtrip

Mar 6

Written By Candice McCoy

Wander Here: Saint Augustine, Florida, USA

We’d been dreaming about Saint Augustine for months and thought it would be just perfect to kick off our adventure around all 50 states in the country’s oldest continuously occupied city…but fate had different plans for us and in the end we had to settle with spending one, way too short day there. You better believe rain or shine we were prepared to pack it in and make the most of it!

History Coming to Life at Castillo de San Marcos National Monument

As we travel around the 50 states, our focus is usually on activities and places that have historical significance, are low cost or preferably free, and of course get us out in nature as much as possible. When you research things to do in Saint Augustine, it’s easy to get distracted by things that don’t fit that description at all - and we may have allllmost gotten sidetracked. But we course corrected and were on our way to a beautiful day despite the moody skies.

Our first stop was a deep dive into history at the Castillo de San Marcos National Monument. It’s a beautiful fort that overlooks the Matanzes River and further out - the Atlantic. It was really brought to life by the period costumes volunteers were wearing as they walked around sharing about the fort’s role in history. We meandered through the halls and of course up to the top where the views were breathtaking. It’s crazy to imagine what it would have been like to be one of the 1500 townspeople who was protected in that fort during the English siege in the 1700’s.

We wandered to the top to see the cannons and check out the views of the river and Saint Augustine. But it wasn’t long before the foreboding clouds began to spill over, and we knew our time was getting cut a bit short! Good thing we got our National Parks passports stamped on the way in 🙂

We raced through the rain to the car, where we decided there was only one clear option of what to do next.

Tacos. We drove across the river and over to Osprey Tacos for shelter and food, and it didn’t not disappoint. Tacos could never be a bad decision.

A Beautiful Encounter with Nature at Anastasia State Park

Next on the docket for our day tour of Saint Augustine was an easy pick.

Anastasia State Park and beach. The red flag was flying and it was rainy and cold, but that didn’t stop us from roaming the beach, breathing in the salt air, collecting all the sea shells, playing in the sand and jumping in the surf. The overcast skies made everything feel a bit mystical, which only added to the beauty.

We basically had to drag the kids away after a couple of hours on the beach. We attempted to do a hike through the state park, but the rain had made the trails so muddy they were almost impassable, so we packed up the car early and headed back to the historic center of town to find some dinner and walk around town.

Saint Augustine: the Oldest and Most Charming City

The energy of Saint Augustine is just special. Wandering the streets with all the quaint shops and restaurants is a whole thing on its own that we could have enjoyed even longer if hadn’t gotten so late and if we hadn’t had a long drive back home.

Saint Augustine stole our hearts as expected, and our only regret is that we weren’t able to spend more time there.