Some trips are meticulously planned. Others just sort of… happen.

This one? A little bit of both.

I found myself heading down to St. Augustine, flying out of Ronald Reagan Washington National Airport—which, for me, is already a departure from the norm. I’m pretty sure it was my first time flying out of Reagan, so right from the start, things felt just different enough to be interesting.

Why St. Augustine?

Part of the reason for the trip was simple: family.

My aunt and uncle happened to be spending about nine days in St. Augustine, and it lined up perfectly with a bit of free time on my end. Any excuse to travel is a good one—but getting to spend time with family along the way? That’s a bonus you don’t pass up.

The other reason? Curiosity.

St. Augustine is the oldest city in the United States, and yet somehow, I realized I didn’t know much about it beyond that one fact. That felt like something worth fixing.

First Impressions (and a Walking Tour Win)

Like any good traveler, I kicked things off with a walking tour—and I’ll say this: those “big picture” tours are always worth it.

They give you the lay of the land, a crash course in history, and just enough context to make everything else you see feel more meaningful. This one didn’t disappoint. Plus, I got to do it alongside my aunt and uncle, which made it even better.

One of the biggest surprises? Flagler College and the story of Henry Flagler—a man who was once one of the richest in America and played a huge role in shaping modern St. Augustine.

I’ll be honest: I had never heard of him before this trip. Turns out, he’s kind of a big deal.

The Fort That Refused to Fall

If there’s one place that really sticks with you, it’s the Castillo de San Marcos.

Originally, the fort was built out of wood… which, as you might imagine, didn’t go so well. Fires took care of that problem more than once. But then came coquina—a building material made of compressed seashells—and everything changed.

Here’s the wild part: cannonballs didn’t shatter the walls. They sank into them.

It’s like the fort was built out of a rock sponge. Absorb the impact, spit it back out later, and keep standing. Which it did—because the fort has never fallen.

They even engineered a tidal-powered waste system (yes, really), where incoming water would flush everything out. Not glamorous, but incredibly smart.

Boats, Fog, and Dolphins

That evening, I hopped on a coastal cruise.

Now, in terms of sightseeing? Not ideal. It was cold. It was foggy. You could barely see a thing.

But honestly? It didn’t matter.

There was music, a bar, some snacks, and just enough atmosphere to make it feel like exactly what I needed—a chance to slow down. And just when it seemed like the view might be a total loss… dolphins showed up.

That alone made it worth it.

Food, Glorious Food

Let’s talk highlights.

Dinner at Prohibition Kitchen delivered a surprisingly great burger and live music to match.

Another night, I met my aunt at Harry’s Seafood Bar & Grille, where we sat outside, listened to music, and I had blackened redfish that absolutely lived up to the hype.

And then there was the Penny Farthing Inn.

Now, I’ve stayed at plenty of places—but this one leans hard into what makes a bed and breakfast special: the breakfast.

Every morning felt like a small event. Thoughtful, well-prepared, and honestly something I looked forward to just as much as anything else on the itinerary.

The Fountain of Youth (and Everything Around It)

The Fountain of Youth Archaeological Park is one of those places that could easily be a one-note attraction—but it’s not.

Yes, the legend is there. And yes, it involves Juan Ponce de León.

But the real value is everything around it.

The park is set up almost like a living history experience—think frontier-style exhibits, people in period clothing, live demonstrations. I watched blacksmiths forging nails, saw muskets fired, and even witnessed a cannon demonstration.

Whether the legend was used to discredit Ponce de León or help fund his expeditions… well, that’s still up for debate.

But the experience itself? Definitely worth it.

Ghosts of the Old City

You can’t visit St. Augustine without hearing about its haunted history.

So naturally, I ended the trip with a nighttime trolley tour through what’s often called one of the most haunted cities in America.

Was it spooky? A little.
Was it fun? Absolutely.

There’s something about riding through an old city at night, hearing stories that blur the line between history and legend—it just works.

The Good Kind of Getaway

By the time I was heading back to the airport early the next morning, I realized something:

This wasn’t a high-intensity, checklist-style trip.

It was something better.

It was walking tours and quiet moments.
Family dinners and unexpected history.
Foggy boat rides that still somehow delivered.

Next up on Mike on the Move — we’re heading across the Atlantic to Copenhagen, Denmark.