St. Augustine: History, Happy Accidents & One Very Good Detour
Updated: 6 hours ago
Day One: Sangria in a Swimming Pool & Oysters on Deviled Eggs
St. Augustine hit me first as a paradox: far larger than I had pictured, yet woven together by a tight, relentless maze of one-way streets.
My instructions were simple enough—pull right up to the St. George Inn, my home base for the next three days, where the staff would help me unload. I found the inn without trouble, but just as I was about to pull up, a city trolley swung around right behind me. Wanting to stay out of the way, I figured I’d just loop around the block.
That simple circle turned into a scenic detour.
After accidentally doing the loop twice, I surrendered, parked in a nearby restaurant lot, and walked over on foot to negotiate a quick trolley-free rescue mission for my luggage.
That little detour paid off immediately. Two young, incredibly welcoming staff members greeted me at the inn, walked back to my car with me, unloaded my bags, and patiently fielded a gazillion questions. There is nothing better than getting a local’s perspective within five minutes of arriving in a new town—especially when the conversation immediately turns to where to eat.
After getting me pointed toward the parking garage and getting me thoroughly excited for the day ahead, they let me know my room wasn't quite ready.
That was music to my ears.
I prefer to start every trip by simply wandering—doing a bit of light reconnaissance, letting my feet lead, and getting a feel for the rhythm of the place.
I headed down Cordova Street with no real destination in mind, just soaking in the historic air.
Before long, luck stepped in: I stumbled directly into one of the scheduled stops on my list. Staring up at the magnificent Lightner Museum, I remembered my stomach was calling the shots—and that the museum happened to have a café.
Stepping inside, the history hit me. The café sits directly in the basin of what was once the world's largest indoor swimming pool during the Gilded Age. On a day that was unexpectedly toasty even for North Florida in late September, sitting at the bottom of an old tiled pool felt deliciously surreal—and wonderfully cool.
I ordered a glass of their housemade sangria and the soup of the day, tomato bisque, and settled in to discover the story behind the stone.
The best part? Once I finished, I could slip straight into the museum galleries without stepping back out into the heat.
It turns out that sitting inside an old swimming pool sipping housemade sangria is actually a rather appropriate way to experience the Lightner. The museum’s backstory is just as eccentric and grand as the building itself.
It all started with Otto C. Lightner, a Chicago newspaper magnate who was so utterly obsessed with collecting that he founded Hobbies magazine. During the Great Depression, as wealthy Gilded Age families were forced to liquidate their sprawling estates, Lightner bought enormous collections of fine art, decorative glass, furniture, and wonderfully quirky curiosities—preserving pieces that might otherwise have disappeared.
By the 1940s, Lightner had accumulated a mountain of treasures and needed somewhere to put them.
Enter Henry Flagler’s abandoned Hotel Alcazar, an 1888 Spanish Renaissance Revival masterpiece that had been closed since the Depression. Lightner purchased the grand hotel, turned it into a museum for his collection, and ultimately left it to the city of St. Augustine.
Leaving the museum behind, I spent the next couple of hours doing what I do best when arriving somewhere new: wandering with absolutely no plan.
I let the streets lead the way until I found myself at the Cathedral Basilica of St. Augustine.
Stepping inside from the bright Florida afternoon, the atmosphere shifted instantly. I was struck by the soaring painted ceiling, stained glass catching the muted light and, most of all, the stillness. Soft hymns played quietly in the background, seeming to anchor the entire space.
I found a pew, sat down, and took a few minutes just to breathe and reflect.
Before leaving, I lit a candle for both of my parents. I watched the tiny flame take hold in the stillness, then stepped back out onto the street feeling a little lighter than when I had walked in.
By then, I knew my room at the St. George Inn would be ready, so I made my way down St. George Street—the pedestrian spine of the historic district and, as I quickly discovered, the place everyone eventually passes through.
It’s unapologetically lively, lined with casual bars, ice-cream counters, souvenir shops and a steady parade of visitors. Not every storefront will call your name, but the people-watching and sheer energy make the street impossible to ignore.
When I arrived at the inn, I discovered that the staff had already carried my luggage up three flights of stairs to my room—a detail I appreciated far more once I saw the climb for myself.
The inn’s rooms are spread among several historic buildings, and elevator access is limited, so anyone who finds stairs challenging should specifically request an elevator-accessible room when booking.
Waiting in the refrigerator was another welcome surprise: a complimentary bottle of crisp, chilled Chardonnay.
Bags delivered and wine cold? Hooray for thoughtful hospitality.
After settling in and taking a moment to unpack, my thoughts turned to dinner.
I had read beforehand that a local spot called Catch 27 served deviled eggs topped with fried oysters. Being the Oklahoma girl I am, the moment I saw that on the menu, I knew there was zero chance I was leaving St. Augustine without trying them.
Catch 27 was just a short, pleasant walk from the hotel. I had booked a table on the outdoor patio, praying the Florida heat would subside by evening. Thankfully, it had cooled down nicely, and the patio was equipped with fans, so breeze or no breeze, comfort wasn't going to be an issue.
I settled in, ordered a vibrant Lavender Haze cocktail, and eagerly awaited those much-anticipated deviled eggs.
My server was a delight—a young girl who was genuinely excited to share the stories behind the restaurant and its dishes. I just sat back, took a sip of my drink, and listened.
This is one of my favorite parts of travel: the unexpected discoveries you only get by talking to the people who live and work there.
She explained that the owner named the restaurant Catch 27 as a nod to Florida being the 27th state admitted to the Union. As for those deviled eggs with fried oysters? They were a new addition from the chef, bringing a bit of Spanish influence to the menu.
They did not disappoint.
Hooked by her enthusiasm, I immediately asked what I should order next.
Without missing a beat, she pointed me toward the blackened shrimp served over crispy grit patties and collard greens. She told me the dish was a tribute to a long-time chef who had recently retired. The recipe had come from his own mama, and the kitchen kept it on the menu to honor his legacy.
Yes, please!
To top it off, she paired the meal with a crisp, beautifully balanced Chenin Blanc that cut right through the richness of the grits.
Content, full, and completely charmed, I made the easy walk back to my room at the St. George Inn—ready for a good night's sleep after a well-spent day.
Day Two: Gilded Age Glamour, Dolphins & a Spooky Nightcap
Day 2 kicked off in the best possible way: breakfast on the patio at Bin 39, the wine bar and café tucked right inside the St. George Inn.
Knowing full well that my day was going to revolve around a continuous string of culinary discoveries, I asked if they could make me a half-order of the Eggs Benedict. They were kind enough to oblige—a small mercy for my appetite, considering I had several meals firmly plotted in my near future.
Fully fueled, I walked over to the majestic Flagler College rotunda for the morning tour.
The place was buzzing, and it quickly became clear I wasn't the only one eager to peek behind those grand doors: every spot on the morning tour was sold out.
Our docent was a vivacious college senior whose enthusiasm for the school was infectious. She began by unravelling the story of the building, which opened in 1888 as Henry Flagler’s Hotel Ponce de Leon, an extravagant winter retreat for Gilded Age society before eventually becoming the centerpiece of Flagler College.
Inside the breathtaking Ladies’ Parlor, she pointed out the Tiffany-blue ceiling and 11 magnificent crystal chandeliers, each reportedly valued in the millions today. The showstopper is a white onyx fireplace and mantle—the largest single piece in the Western Hemisphere. Nestled inside the mantle is an early electric clock made by Thomas Edison.
The funny part? The clock apparently doesn’t work terribly often.
When you’re surrounded by that much splendor, nobody seems particularly bothered.
What fascinated me most was the sheer ambition behind the place. Flagler's enormous hotel was completed in just 18 months, designed by two young architects, John Carrère and Thomas Hastings, early in their careers. They would later go on to design the New York Public Library.
Flagler was also fascinated by electricity and enlisted his friend Thomas Edison to help bring electric power to the hotel at a time when the technology was still astonishingly new. Imagine checking into a grand resort in the 1800s and encountering electric lights for the first time.
The Ponce de Leon had roughly 300 guest rooms and catered to wealthy winter visitors who arrived for an entire season rather than a long weekend. And for all the grandeur, the hotel operated for only a few months each year.
Apparently, even Gilded Age excess had a season.
After the tour, I headed back outside with no particular agenda—which, by now, was becoming my favorite way to experience St. Augustine.
This is the ultimate city for wandering, the kind of place where the best discoveries seem to be tucked down narrow lanes or hiding behind ornate, slightly weathered iron gates. I spent the afternoon meandering along Aviles, Charlotte, and King Streets, stopping whenever something caught my eye.
It was surprisingly hot for October 1st, but St. Augustine had already decided it was most definitely fall.
Halloween decorations were everywhere.
I quickly learned that this town takes spooky season seriously. And almost as soon as Halloween ends, St. Augustine rolls straight into its famous Nights of Lights celebration, when the historic district is covered in millions of tiny white lights and the holiday crowds descend.
I quietly congratulated myself on slipping into town during that little sweet spot in between.
By late afternoon, my friend from Amelia Island arrived to join me for a sunset cruise with Florida Water Tours. We cast off promptly at 6:00 PM with about twenty other guests on board.
And then nature took over.
A tree hugging the side of the turret of the Castillo Tracey & Jenn on the sunset cruise St. Augustine Riding past the lighthouse on the sunset cruise
Pelicans dive-bombed into the water in search of dinner while dolphins surfaced around us in pods, occasionally leaping and gliding alongside the boat. As the sun began its slow descent, the sky shifted through increasingly vivid shades of orange, pink, and purple.
Sunset Cruise St. Augustine Castillo at sunset St. Augustine Giant cross at sunset St. Augustine
You couldn't have ordered a more postcard-perfect Florida sunset if you’d tried.
After our 90-minute cruise, we called an Uber and headed to Forgotten Tonic, a local spot that had been recommended to me more than once.
Halloween caught up with us before we even arrived.
Our driver's entire SUV had been transformed for the season, complete with colored LED lights wrapped around the ceiling, cobwebs, and enormous plastic spiders.
This town truly does not mess around when it comes to October.
When we stepped inside Forgotten Tonic, the transformation continued. The entire restaurant had gone all-in on Halloween. We grabbed two seats at the bar and discovered that even the cocktail glassware had joined the party.
Forgotten Tonic St. Augustine Bar glasses for halloween Forgotten Tonic Cheers at Forgotten Tonic
If you are a fan of all things spooky, I may have found your holy grail.
We toasted to a fabulous day, lingering over our drinks, the atmosphere, and the easy conversation.
Gilded Age glamour in the morning. Dolphins at sunset. Giant plastic spiders by night.
Day 2 ended with a whole bucket of delightful surprises—just the way I like it.
Day Three: 213 Steps, A Little Rain & One Last Toast
Day 3 began out in the quiet courtyard at the St. George Inn, savoring a delicious breakfast sandwich and a hot cup of coffee.
Bin 39 courtyard Breakfast sandwich at Bin 39
Today’s adventure required retrieving my car from the garage, because I was heading across the Bridge of Lions to Anastasia Island to explore the iconic St. Augustine Lighthouse and nearby Anastasia State Park.
Looking up, I noticed the morning sky was already gathering heavy black-and-grey storm clouds.
Fingers crossed. Surely they could hold off until afternoon.
When I bought my lighthouse ticket, the attendant gave me a quick warning: if lightning was detected nearby, they'd close the tower immediately.
All right, then. No time to waste.
The climb to the top is 219 steps, and someone with a sense of humor clearly understood that distraction would be helpful. The winding staircase is dotted with trivia, step counts, and even calorie information.
St. Augustine Lighthouse Stairs going down in the lighthouse
I have to admit, the calorie math was deeply disappointing.
All that climbing for how many calories?
Thankfully, the reward at the top made every step worthwhile. The 360-degree view is spectacular, stretching across Anastasia Island and the surrounding waterways with historic St. Augustine visible in the distance.
Top of the Lighthouse St. Augustine Tracey at the top of the lighthouse
Back at sea level, I took my time exploring the keeper's house and the maritime history scattered throughout the grounds. You absolutely don’t have to climb the tower to enjoy the lighthouse, but if you’re physically able and the weather cooperates, do it.
I headed back across the bridge and grabbed a late lunch at Mojo Old City BBQ, happily settling onto the patio. The drizzle had taken the edge off the Florida heat, and I sat there watching the sightseeing trolleys roll past while doing some very important barbecue research.
Exterior MOJO BBQ St. Augustine Sloppy Mojo sandwich at MOJO BBQ
With my belly full, the afternoon called for—you guessed it—more unstructured wandering.
That’s when I happened upon the Peña-Peck House.
Exterior of the Pena-Peck House Back gardens at the Pena-Peck house
Built during St. Augustine’s Spanish colonial period for royal treasurer Juan Esteban de Peña, the house eventually came into the Peck family. But the part of its story that captured me belonged to Anna Gardner Burt, Dr. Seth Peck’s granddaughter.
When Anna died in 1931, she left the historic house to the city of St. Augustine with a very particular purpose. Since the following year, the property has been cared for by the Women’s Exchange of St. Augustine.
Today, you can tour the historic rooms and browse a small shop filled with handmade goods, but what stayed with me was the mission behind it. The Women’s Exchange continues its tradition of supporting women through educational scholarships and community programs.
Desk at Pena Peck House Chest used to carry coin during Pena days Indoor plumbing Anna Peck
I’d wandered in because an old house caught my eye.
I walked out thinking about generations of women quietly helping other women build something for themselves.
By late afternoon, the threatened rain finally arrived, soft and steady, cooling the cobblestones and forcing the entire city—and me—to slow down.
Had I not already spent a warm afternoon happily tucked inside the air-conditioned grandeur of the Lightner Museum, this would have been ideal museum weather. Someone even suggested the wonderfully bizarre-sounding Medieval Torture Museum.
With the rain easing and the cooler air settling over town, I walked over to River & Fort for my final evening in St. Augustine. Still pleasantly satisfied from my late barbecue lunch, I decided to make dinner out of small plates and a very good glass of wine on the rooftop overlooking the Castillo de San Marcos and Matanzas Bay.
I started with a crisp French 75 and a half-dozen local oysters—medium-sized, wonderfully sweet, and served with bright mignonette.
Then came the Cannonball Shrimp: crispy rice noodles, sweet shrimp, bacon, sesame and a rich, tangy sauce.
Fresh oysters at River & Fort St. Augustine Cannonball shrimp at River & Fort St. Augustine
And because this was my last night, there was really only one appropriate accompaniment: a perfectly chilled glass of one of my favorite white wines, ZD Chardonnay.
Sitting there above the bayfront, watching the last light settle over the Castillo, I thought back to my first few minutes in St. Augustine three days earlier—circling one-way streets with a trolley behind me and absolutely no idea what I was getting myself into.
I’d come expecting history. And there was plenty of it: Flagler’s Gilded Age extravagance, Spanish colonial houses, old churches, lighthouses, and streets that have been carrying people through this city for centuries.
What I hadn’t expected was how much fun I’d have in between all that history.
Sangria in an old swimming pool. A candle lit in a silent cathedral. Fried oysters on deviled eggs. Dolphins at sunset. A Halloween-crazed Uber. 219 lighthouse steps. A historic house I discovered simply because I turned down the right street.
And maybe that’s what I’ll remember most about St. Augustine.
Yes, you should come for the history. But don’t schedule every minute of it.
Leave yourself an hour to kill. Take the wrong turn. Talk to the person behind the bar. Duck through the gate that catches your eye.
Because in a city this old, some of the best stories are the ones you weren’t looking for.
Where to Stay in St. Augustine
Historic inns, waterfront stays, and polished hotels—I've rounded up six St. Augustine properties I'd put on my own shortlist for location, character, and atmosphere.
There's More to St. Augustine...
Loved the story? My complete Tracey's Tastes Guide to St. Augustine is coming soon—with favorite tables, charming stays, hidden gems, and curated itineraries to help you explore the city your way.
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